No renderable structure data available
O1B(C2C=CC(=CC=2C)N)OC(C)(C)C1(C)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-AMINO-2-METHYLPHENYLBORONIC ACID, PINACOL ESTER |
|---|---|
| IUPAC Name | — |
| CAS Number | 631911-01-8 |
| Database ID | 17750210 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-AMINO-2-METHYLPHENYLBORONIC ACID, PINACOL ESTER (CAS 631911-01-8) 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 17750210
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8c3cc46243fd43a79909728d2cfc2d6cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8c3cc46243fd43a79909728d2cfc2d6cConditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an oven-dried round bottom flask fitted with a stir bar was added 4-bromo-3-methylaniline (5.7 gm, 31 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.3 mL, 92 mmol, Aldrich Chemical Company), and PdCl2(PPh3)2 (2.2 gm, 3.1 mmol, Strem Chemicals Inc, Newburyport, Mass.). The flask was sealed with a rubber septum, purged with Argon, and then charged with dry dioxane (100 mL) and triethylamine (26 mL). The reaction mixture was stirred vigorously at 95° C. for 16 h. After cooling to rt, the dioxane was removed in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL), and was dried over MgSO4. Removal of the solvents in vacuo followed by flash chromatography of the residue yielded the product (3.3 gm, 46%) as a tan oil. 1H-NMR (CDCl3; 400 MHz): δ 7.61–7.64 (m, 1H), 6.48–6.58 (m, 2H), 3.60–3.90, (br s, 2H), 2.49 (s, 3H), 1.34 (s, 12H). ESI-MS (m/z): Calcd. for C13H20BNO2: 234.1 (M+H); found: 234.2 To an oven-dried round bottom flask fitted with a stir bar The flask was sealed with a rubber septum purged with Argon charged with dry dioxane (100 mL) and triethylamine (26 mL) After cooling to rt the dioxane was removed in vacuo the residue was partitioned between EtOAc (200 mL) and water (100 mL) The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL) was dried over MgSO4 Removal of the solvents in vacuo
Source ID: ord-3e263c8cddd04b0bad7e8eb42e91f4efConditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an oven-dried round bottom flask fitted with a stir bar was added 4-bromo-3-methylaniline (5.7 gm, 31 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.3 mL, 92 mmol, Aldrich Chemical Company), and PdCl2(PPh3)2 (2.2 gm, 3.1 mmol, Strem Chemicals Inc, Newburyport, Mass.). The flask was sealed with a rubber septum, purged with Argon, and then charged with dry dioxane (100 mL) and triethylamine (26 mL). The reaction mixture was stirred vigorously at 95° C. for 16 h. After cooling to rt, the dioxane was removed in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL), and was dried over MgSO4. Removal of the solvents in vacuo followed by flash chromatography of the residue yielded the product (3.3 gm, 46%) as a tan oil. 1H-NMR (CDCl3; 400 MHz): δ 7.61–7.64 (m, 1H), 6.48–6.58 (m, 2H), 3.60–3.90, (br s, 2H), 2.49 (s, 3H), 1.34 (s, 12H). ESI-MS (m/z): Calcd. for C13H20BNO2: 234.1 (M+H); found: 234.2 To an oven-dried round bottom flask fitted with a stir bar The flask was sealed with a rubber septum purged with Argon charged with dry dioxane (100 mL) and triethylamine (26 mL) After cooling to rt the dioxane was removed in vacuo the residue was partitioned between EtOAc (200 mL) and water (100 mL) The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL) was dried over MgSO4 Removal of the solvents in vacuo
Source ID: ord-d5bc7358789144aa9b590508f02c2f6fConditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an oven-dried round bottom flask fitted with a stir bar was added 4-bromo-3-methylaniline (5.7 gm, 31 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.3 mL, 92 mmol, Aldrich Chemical Company), and PdCl2(PPh3)2 (2.2 gm, 3.1 mmol, Strem Chemicals Inc, Newburyport, Mass.). The flask was sealed with a rubber septum, purged with Argon, and then charged with dry dioxane (100 mL) and triethylamine (26 mL). The reaction mixture was stirred vigorously at 95° C. for 16 h. After cooling to rt, the dioxane was removed in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL), and was dried over MgSO4. Removal of the solvents in vacuo followed by flash chromatography of the residue yielded the product (3.3 gm, 46%) as a tan oil. 1H-NMR (CDCl3; 400 MHz): δ 7.61–7.64 (m, 1H), 6.48–6.58 (m, 2H), 3.60–3.90, (br s, 2H), 2.49 (s, 3H), 1.34 (s, 12H). ESI-MS (m/z): Calcd. for C13H20BNO2: 234.1 (M+H); found: 234.2 To an oven-dried round bottom flask fitted with a stir bar The flask was sealed with a rubber septum purged with Argon charged with dry dioxane (100 mL) and triethylamine (26 mL) After cooling to rt the dioxane was removed in vacuo the residue was partitioned between EtOAc (200 mL) and water (100 mL) The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL) was dried over MgSO4 Removal of the solvents in vacuo
Source ID: ord-d5bc7358789144aa9b590508f02c2f6fConditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an oven-dried round bottom flask fitted with a stir bar was added 4-bromo-3-methylaniline (5.7 gm, 31 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.3 mL, 92 mmol, Aldrich Chemical Company), and PdCl2(PPh3)2 (2.2 gm, 3.1 mmol, Strem Chemicals Inc, Newburyport, Mass.). The flask was sealed with a rubber septum, purged with Argon, and then charged with dry dioxane (100 mL) and triethylamine (26 mL). The reaction mixture was stirred vigorously at 95° C. for 16 h. After cooling to rt, the dioxane was removed in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL), and was dried over MgSO4. Removal of the solvents in vacuo followed by flash chromatography of the residue yielded the product (3.3 gm, 46%) as a tan oil. 1H-NMR (CDCl3; 400 MHz): δ 7.61–7.64 (m, 1H), 6.48–6.58 (m, 2H), 3.60–3.90, (br s, 2H), 2.49 (s, 3H), 1.34 (s, 12H). ESI-MS (m/z): Calcd. for C13H20BNO2: 234.1 (M+H); found: 234.2 To an oven-dried round bottom flask fitted with a stir bar The flask was sealed with a rubber septum purged with Argon charged with dry dioxane (100 mL) and triethylamine (26 mL) After cooling to rt the dioxane was removed in vacuo the residue was partitioned between EtOAc (200 mL) and water (100 mL) The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL) was dried over MgSO4 Removal of the solvents in vacuo
Source ID: ord-d5bc7358789144aa9b590508f02c2f6fConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium carbonate (224 mg, 1.619 mmol) was added to a mixture of ((S)-1-{(S)-2-[4-(4-bromo-3-methyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (150 mg, 0.324 mmol) and 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (90.6 mg, 0.389 mmol) in toluene (0.6 mL, 6 mmol) and water (0.3 mL, 20 mmol). The reaction mixture was degassed and flushed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (44.9 mg, 0.039 mmol) was added under nitrogen and then the reaction mixture was capped and heated at 100° C. overnight, cooled to RT and partitioned between ethyl acetate (10 mL) and water (2 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to give a brownish oil, which was purified by silica gel chromatography (12 g silica gel, 0-100% EtOAc/hexanes). Desired fractions were combined and concentrated to give the title compound as a light yellowish foam (135 mg, 85% yield). (m/z): [M+H]+ calcd for C28H35N5O3 490.27 found 490.6. The reaction mixture was degassed flushed with nitrogen the reaction mixture was capped cooled to RT partitioned between ethyl acetate (10 mL) and water (2 mL) The organic layer was dried over sodium sulfate filtered concentrated to give a brownish oil, which was purified by silica gel chromatography (12 g silica gel, 0-100% EtOAc/hexanes) concentrated
Source ID: ord-19eddfd936dd412093e0d5b1815d268bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Method as described for intermediate 5 using (S)-4-(2-chloro-7-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 13) and 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting materials. The mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and solvent removed in vacuo. The residue was purified by triturating with a (9:1) mixture of petrol ether (40-60)/ethyl acetate, yielding the title compound after filtration and drying of the solid obtained (85 mg, 0.24 mmol, 68%). The mixture was filtered through a celite 545 pre-packed cartridge (2.5 g) washed with MeOH and solvent removed in vacuo The residue was purified by triturating with a (9:1) mixture of petrol ether (40-60)/ethyl acetate
Source ID: ord-306caf0d69574a1485600a9b3a00c75dConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium carbonate (224 mg, 1.619 mmol) was added to a mixture of ((S)-1-{(S)-2-[4-(4-bromo-3-methyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (150 mg, 0.324 mmol) and 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (90.6 mg, 0.389 mmol) in toluene (0.6 mL, 6 mmol) and water (0.3 mL, 20 mmol). The reaction mixture was degassed and flushed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (44.9 mg, 0.039 mmol) was added under nitrogen and then the reaction mixture was capped and heated at 100° C. overnight, cooled to RT and partitioned between ethyl acetate (10 mL) and water (2 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to give a brownish oil, which was purified by silica gel chromatography (12 g silica gel, 0-100% EtOAc/hexanes). Desired fractions were combined and concentrated to give the title compound as a light yellowish foam (135 mg, 85% yield). (m/z): [M+H]+ calcd for C28H35N5O3 490.27 found 490.6. The reaction mixture was degassed flushed with nitrogen the reaction mixture was capped cooled to RT partitioned between ethyl acetate (10 mL) and water (2 mL) The organic layer was dried over sodium sulfate filtered concentrated to give a brownish oil, which was purified by silica gel chromatography (12 g silica gel, 0-100% EtOAc/hexanes) concentrated
Source ID: ord-ccdbd4a788914211af4830510d60c7d3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Intermediate 26A (1 g, 3.80 mmol), ammonium chloride (1.432 g, 26.6 mmol), and zinc (1.491 g, 22.81 mmol) were added to a flask, followed by the addition of EtOH (10.0 mL) and THF (10.0 mL). The reaction mixture was stirred at room temperature for 2 hours and filtered through a pad of CELITE®. The filtrate was concentrated under reduced pressure to yield Intermediate 26 (885 mg, 100% yield). MS (ES): m/z=234.2 [M+H]+. filtered through a pad of CELITE® The filtrate was concentrated under reduced pressure
Source ID: ord-de51050d302846bb909eac369cec786fConditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an oven-dried round bottom flask fitted with a stir bar was added 4-bromo-3-methylaniline (5.7 gm, 31 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.3 mL, 92 mmol, Aldrich Chemical Company), and PdCl2(PPh3)2 (2.2 gm, 3.1 mmol, Strem Chemicals Inc, Newburyport, Mass.). The flask was sealed with a rubber septum, purged with Argon, and then charged with dry dioxane (100 mL) and triethylamine (26 mL). The reaction mixture was stirred vigorously at 95° C. for 16 h. After cooling to rt, the dioxane was removed in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL), and was dried over MgSO4. Removal of the solvents in vacuo followed by flash chromatography of the residue yielded the product (3.3 gm, 46%) as a tan oil. 1H-NMR (CDCl3; 400 MHz): δ 7.61–7.64 (m, 1H), 6.48–6.58 (m, 2H), 3.60–3.90, (br s, 2H), 2.49 (s, 3H), 1.34 (s, 12H). ESI-MS (m/z): Calcd. for C13H20BNO2: 234.1 (M+H); found: 234.2 To an oven-dried round bottom flask fitted with a stir bar The flask was sealed with a rubber septum purged with Argon charged with dry dioxane (100 mL) and triethylamine (26 mL) After cooling to rt the dioxane was removed in vacuo the residue was partitioned between EtOAc (200 mL) and water (100 mL) The organic layer was washed with saturated NaHCO3 (2×75 mL), brine (50 mL) was dried over MgSO4 Removal of the solvents in vacuo
Source ID: ord-3e263c8cddd04b0bad7e8eb42e91f4efPubChem References
These sources are listed in the compound's public database record.
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