No renderable structure data available
C1=CC(=C2C(=C1OC(F)(F)F)C=CN2)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 7-fluoro-4-(trifluoromethoxy)-1H-indole |
|---|---|
| IUPAC Name | — |
| CAS Number | 1208977-14-3 |
| Database ID | 46175564 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
7-fluoro-4-(trifluoromethoxy)-1H-indole (CAS 1208977-14-3) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 46175564
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b5647ab077b247f3b7b65260f5059621Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5 (16 g, 72.8 mmol) and powder KOH (20.4 g, 364.2 mmol) in DMSO (150 mL) is stirred at rt for 10 min. 2-Methoxyethyl bromide (10.3 mL, 109.2 mmol) is added. This mixture is stirred at rt overnight. LC/MS indicates the reaction is completed. The mixture is partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer is extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant to give 19.3 g (95%) of 6 as a yellow liquid. 1H NMR (CDCl3) δ 7.15 (d, J=2.1 Hz, 1H), 6.90-6.75 (m, 2H), 6.56 (t, J=2.5 Hz, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.72 (t, J=5.2 Hz, 2H), 3.31 (s, 3H); 19F NMR (CDCl3) δ −57.54 (s, 3F), −137.00 (d, J=11.3 Hz, 1F); MS 278 (M+1, 100%). This mixture is stirred at rt overnight The mixture is partitioned between H2O and Et2O The two layers are separated the aqueous layer is extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant
Source ID: ord-982fdaf4a1d34035be5e0cad47ad5fafConditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4 (28.9 g, 79.6 mmol) and KOH (35.7 g, 636.7 mmol) in degassed t-BuOH (300 mL) is heated at 70° C. overnight. LC/MS indicates the reaction is completed. The mixture is cooled to rt, and then partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer was extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant to give 16 g (91%) of 5 as a yellow liquid. 1H NMR (CDCl3) δ 8.47 (br s, 1H), 7.35-7.20 (m, 1H), 6.95-6.80 (m, 2H), 6.68 (d, J=2.5 Hz, 1H); 19F NMR (CDCl3) δ −57.63 (s, 3F), −136.10 (d, J=8.5 Hz, 1F); MS 220 (M+1, 100%), 200. The mixture is cooled to rt partitioned between H2O and Et2O The two layers are separated the aqueous layer was extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant
Source ID: ord-8b8084eefe2d4b58ac9bc2e07cd5a38fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5 (16 g, 72.8 mmol) and powder KOH (20.4 g, 364.2 mmol) in DMSO (150 mL) is stirred at rt for 10 min. 2-Methoxyethyl bromide (10.3 mL, 109.2 mmol) is added. This mixture is stirred at rt overnight. LC/MS indicates the reaction is completed. The mixture is partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer is extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant to give 19.3 g (95%) of 6 as a yellow liquid. 1H NMR (CDCl3) δ 7.15 (d, J=2.1 Hz, 1H), 6.90-6.75 (m, 2H), 6.56 (t, J=2.5 Hz, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.72 (t, J=5.2 Hz, 2H), 3.31 (s, 3H); 19F NMR (CDCl3) δ −57.54 (s, 3F), −137.00 (d, J=11.3 Hz, 1F); MS 278 (M+1, 100%). This mixture is stirred at rt overnight The mixture is partitioned between H2O and Et2O The two layers are separated the aqueous layer is extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant
Source ID: ord-caeaad45c57f408eada70977fc0ca9dcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5 (16 g, 72.8 mmol) and powder KOH (20.4 g, 364.2 mmol) in DMSO (150 mL) is stirred at rt for 10 min. 2-Methoxyethyl bromide (10.3 mL, 109.2 mmol) is added. This mixture is stirred at rt overnight. LC/MS indicates the reaction is completed. The mixture is partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer is extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant to give 19.3 g (95%) of 6 as a yellow liquid. 1H NMR (CDCl3) δ 7.15 (d, J=2.1 Hz, 1H), 6.90-6.75 (m, 2H), 6.56 (t, J=2.5 Hz, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.72 (t, J=5.2 Hz, 2H), 3.31 (s, 3H); 19F NMR (CDCl3) δ −57.54 (s, 3F), −137.00 (d, J=11.3 Hz, 1F); MS 278 (M+1, 100%). This mixture is stirred at rt overnight The mixture is partitioned between H2O and Et2O The two layers are separated the aqueous layer is extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant
Source ID: ord-caeaad45c57f408eada70977fc0ca9dcConditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4 (28.9 g, 79.6 mmol) and KOH (35.7 g, 636.7 mmol) in degassed t-BuOH (300 mL) is heated at 70° C. overnight. LC/MS indicates the reaction is completed. The mixture is cooled to rt, and then partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer was extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant to give 16 g (91%) of 5 as a yellow liquid. 1H NMR (CDCl3) δ 8.47 (br s, 1H), 7.35-7.20 (m, 1H), 6.95-6.80 (m, 2H), 6.68 (d, J=2.5 Hz, 1H); 19F NMR (CDCl3) δ −57.63 (s, 3F), −136.10 (d, J=8.5 Hz, 1F); MS 220 (M+1, 100%), 200. The mixture is cooled to rt partitioned between H2O and Et2O The two layers are separated the aqueous layer was extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant
Source ID: ord-d8279f7518f74254ab257a8dd223c69dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b5647ab077b247f3b7b65260f5059621Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5 (16 g, 72.8 mmol) and powder KOH (20.4 g, 364.2 mmol) in DMSO (150 mL) is stirred at rt for 10 min. 2-Methoxyethyl bromide (10.3 mL, 109.2 mmol) is added. This mixture is stirred at rt overnight. LC/MS indicates the reaction is completed. The mixture is partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer is extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant to give 19.3 g (95%) of 6 as a yellow liquid. 1H NMR (CDCl3) δ 7.15 (d, J=2.1 Hz, 1H), 6.90-6.75 (m, 2H), 6.56 (t, J=2.5 Hz, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.72 (t, J=5.2 Hz, 2H), 3.31 (s, 3H); 19F NMR (CDCl3) δ −57.54 (s, 3F), −137.00 (d, J=11.3 Hz, 1F); MS 278 (M+1, 100%). This mixture is stirred at rt overnight The mixture is partitioned between H2O and Et2O The two layers are separated the aqueous layer is extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant
Source ID: ord-a242b3324fee4bc1a1c57baa585c793fConditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4 (28.9 g, 79.6 mmol) and KOH (35.7 g, 636.7 mmol) in degassed t-BuOH (300 mL) is heated at 70° C. overnight. LC/MS indicates the reaction is completed. The mixture is cooled to rt, and then partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer was extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant to give 16 g (91%) of 5 as a yellow liquid. 1H NMR (CDCl3) δ 8.47 (br s, 1H), 7.35-7.20 (m, 1H), 6.95-6.80 (m, 2H), 6.68 (d, J=2.5 Hz, 1H); 19F NMR (CDCl3) δ −57.63 (s, 3F), −136.10 (d, J=8.5 Hz, 1F); MS 220 (M+1, 100%), 200. The mixture is cooled to rt partitioned between H2O and Et2O The two layers are separated the aqueous layer was extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant
Source ID: ord-62b625a4860646ceb58cdb6d4504dd78Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5 (16 g, 72.8 mmol) and powder KOH (20.4 g, 364.2 mmol) in DMSO (150 mL) is stirred at rt for 10 min. 2- Methoxyethyl bromide (10.3 mL, 109.2 mmol) is added. This mixture is stirred at rt overnight. LC/MS indicates the reaction is completed. The mixture is partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer is extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant to give 19.3 g (95%) of 6 as a yellow liquid. 1H NMR (CDCl3) δ 7.15 (d, J=2.1 Hz, 1H), 6.90-6.75 (m, 2H), 6.56 (t, J=2.5 Hz, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.72 (t, J=5.2 Hz, 2H), 3.31 (s, 3H); 19F NMR (CDCl3) δ −57.54 (s, 3F), −137.00 (d, J=11.3 Hz, 1F); MS 278 (M+1, 100%). This mixture is stirred at rt overnight The mixture is partitioned between H2O and Et2O The two layers are separated the aqueous layer is extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant
Source ID: ord-555ff9f5ba6c4e56a498877c4407a699Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4 (28.9 g, 79.6 mmol) and KOH (35.7 g, 636.7 mmol) in degassed t-BuOH (300 mL) is heated at 70° C. overnight. LC/MS indicates the reaction is completed. The mixture is cooled to rt, and then partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer was extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant to give 16 g (91%) of 5 as a yellow liquid. 1H NMR (CDCl3) δ 8.47 (br s, 1H), 7.35-7.20 (m, 1H), 6.95-6.80 (m, 2H), 6.68 (d, J=2.5 Hz, 1H); 19F NMR (CDCl3) δ −57.63 (s, 3F), −136.10 (d, J=8.5 Hz, 1F); MS 220 (M+1, 100%), 200. The mixture is cooled to rt partitioned between H2O and Et2O The two layers are separated the aqueous layer was extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant
Source ID: ord-3be34982a19f4fda80251739270a9e73Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 5 (16 g, 72.8 mmol) and powder KOH (20.4 g, 364.2 mmol) in DMSO (150 mL) is stirred at rt for 10 min. 2-Methoxyethyl bromide (10.3 mL, 109.2 mmol) is added. This mixture is stirred at rt overnight. LC/MS indicates the reaction is completed. The mixture is partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer is extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant to give 19.3 g (95%) of 6 as a yellow liquid. 1H NMR (CDCl3) δ 7.15 (d, J=2.1 Hz, 1H), 6.90-6.75 (m, 2H), 6.56 (t, J=2.5 Hz, 1H), 3.72 (t, J=5.2 Hz, 2H), 3.72 (t, J=5.2 Hz, 2H), 3.31 (s, 3H); 19F NMR (CDCl3) δ −57.54 (s, 3F), −137.00 (d, J=11.3 Hz, 1F); MS 278 (M+1, 100%). This mixture is stirred at rt overnight The mixture is partitioned between H2O and Et2O The two layers are separated the aqueous layer is extracted with Et2O (2×) The combined organic layers are washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The crude material is purified on silica gel with heptane/EtOAc (100/0 to 50/50) as eluant
Source ID: ord-982fdaf4a1d34035be5e0cad47ad5fafPubChem References
These sources are listed in the compound's public database record.
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