2,3-dihydro-1-benzofuran-3-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, MS: m/e=454.3 (M+H+), was prepared in accordance with the general method of example 13 from 5-nitro-2-chloroquinoline, 3,5-difluorobenzenesulfonyl chloride and rac-2,3-dihydro-benzofuran-3-ylamine (CAS 109926-35-4).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, MS: m/e=436.1 (M+H+), was prepared in accordance with the general method of example 13 from 5-nitro-2-chloroquinoline, 4-fluorobenzenesulfonyl chloride and rac-2,3-dihydro-benzofuran-3-ylamine (CAS 109926-35-4).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, MS: m/e=369.0 (M+H+), was prepared in accordance with the general method of example 6 from 5-iodo-2-chloroquinoline, rac-2,3-dihydro-benzofuran-3-ylamine (CAS 109926-35-4) and 3-(aminomethyl)pyridine.

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-(2-Chloro-quinolin-5-yl)-3,4,5-trifluoro-benzenesulfonamide (150 mg, 0.402 mmol) was dissolved in 5 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. rac-2,3-Dihydro-benzofuran-3-ylamine (CAS 109926-35-4, 82 mg, 0.607 mmol), sodium tert.-butylate (97 mg, 1.01 mmol), 1,1′-bis(diphenylphosphin)ferrocen (33 mg, 0.06 mmol) and 1,1′-bis(diphenylphosphin)ferrocen-palladium(II) chloride (16 mg, 0.02 mmol) were added. The reaction mixture was stirred in a sealed tube at 120° C. for 6 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->70:30 gradient). The title compound was obtained as a yellow foam (100 mg, 53%), MS: m/e 472.4 (M+H+). Argon was bubbled through the solution for 2 minutes to remove oxygen The solvent was evaporated the residue purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->70:30 gradient)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2,3-Dihydro-benzofuran-3-yl)-(6-nitro-quinolin-2-yl)-amine was prepared according to step A in general example 2 from 2-chloro-6-nitro-quinoline and 2,3-dihydro-benzofuran-3-ylamine (CAS no.: 109926-23-4); MS: m/e=308.3 (M+H+).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solution of benzofuran-3(2H)-one oxime (1.0 g, obtained from commercially available benzofuran-3(2H)-one via the procedure outlined for the synthesis of 4-fluorobenzofuran-3(2H)-one oxime from 4-fluorobenzofuran-3(2H)-one) in 50 mL MeOH, 10% Palladium on active carbon (0.1 g) was added. The mixture was evacuated then filled with H2 three times. Finally the oxime was reduced under a H2 balloon for 24 hours. The mixture was filtered through a pad of celite, and the cake was washed with MeOH twice. After removing the solvents under vacuum, 0.99 g brown-yellow residue was obtained as the desired amine. 1H NMR (300 MHz, CDCl3): δ 7.32 (d, 1H), 7.19 (t, 1H), 6.94 (t, 1H), 6.82 (d, 1H), 4.5-4.7 (m, 1H), 4.64 (s, 1H), 4.1-4.2 (m, 1H). The mixture was evacuated then filled with H2 three times for 24 hours The mixture was filtered through a pad of celite the cake was washed with MeOH twice After removing the solvents under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solution of benzofuran-3(2H)-one oxime (1.0 g, obtained from commercially available benzofuran-3(2H)-one via the procedure outlined for the synthesis of 4-fluorobenzofuran-3(2H)-one oxime from 4-fluorobenzofuran-3(2H)-one) in 50 mL MeOH, 10% Palladium on active carbon (0.1 g) was added. The mixture was evacuated then filled with H2 three times. Finally the oxime was reduced under a H2 balloon for 24 hours. The mixture was filtered through a pad of celite, and the cake was washed with MeOH twice. After removing the solvents under vacuum, 0.99 g brown-yellow residue was obtained as the desired amine. 1H NMR (300 MHz, CDCl3): δ 7.32 (d, 1H), 7.19 (t, 1H), 6.94 (t, 1H), 6.82 (d, 1H), 4.5-4.7 (m, 1H), 4.64 (s, 1H), 4.1-4.2 (m, 1H). The mixture was evacuated then filled with H2 three times for 24 hours The mixture was filtered through a pad of celite the cake was washed with MeOH twice After removing the solvents under vacuum