Sodium Carbonate → 4-Amino-3-(4-aminophenyl)-furo[3,2-c]pyridine

HRID 734307Notes

Reaction equation

[NH2:1][C:2]1[C:7]2[C:8](Br)=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:7]2[C:8]([C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 4-amino-3-bromo-furo[3,2-c]pyridine (7) (63 mg, 0.29 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (84 mg, 0.38 mmol), Pd(PPh3)4 (34 mg, 0.029 mmol) and sodium carbonate (0.74 ml, 1.5 mmol) in 3 ml of DME was stirred for 14 hours at 80° C. The solvent was removed, and the resultant residue was purified by chromatography on a silica gel column gel to afford the titled compound (55 mg) 1H NMR (400 MHz, DMSO-d6) ppm 7.82 (d, J=6.1 Hz, 1H), 7.77 (s, 1H), 7.15 (d, J=8.3 Hz, 2H), 6.89 (d, J=5.8 Hz, 1H), 6.69 (d, J=8.3 Hz, 2H), 5.49 (s, 2H), 5.32 (s, 2H). MS: m/z 226 (M+H)+.

Workup

customThe solvent was removed
customthe resultant residue was purified by chromatography on a silica gel column gel

Sources & evidence

ORD record: ord-76fb99d7402c44419ecb7c38472bd4eb
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592352B2

Reaction notes

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