4-Chlorophenylboronic acid → HCID 11177814, compound

HRID 734315Notes

Reaction equation

[NH2:1][C:2]1[C:7]2[C:8](Br)=[CH:9][S:10][C:6]=2[C:5]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[CH:4][N:3]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)(O)[O-].[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:28]3[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=3)=[CH:9][S:10][C:6]=2[C:5]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 4-amino-3-bromo-7-(3,4,5-trimethoxyphenyl)-thieno[3,2-c]pyridine (30 mg, 0.076 mmol), Pd(PPh3)4 (17 mg, 10 mol %), 4-chlorobenzeneboronic acid (30 mg, 0.19 mmol) and 2M sodium bicarbonate (0.19 ml, 0.38 mmol) in DME (2 ml) was stirred for 14 hours at 80° C. The crude mixture was directly applied to SCX (Varian, 5 g) and eluted with 1N NH3 in CHCl3 and MeOH. The eluant was collected and concentrated in vacuo. The residue was purified by chromatography on a silica gel column to afford the titled compound (15.5 mg) 1H NMR (400 MHz, DMSO-d6) ppm 7.99 (s, 1H), 7.60 (d, J=8.6 Hz, 2H), 7.58 (s, 1H), 7.51 (d, J=7.3 Hz, 2H), 6.95 ((s, 2H), 5.47 (s, 2H), 3.85 (s, 6H), 3.73 (s, 3H). MS: m/z 427, 429 (M+H)+.

Workup

washeluted with 1N NH3 in CHCl3 and MeOH
customThe eluant was collected
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-adb79b7d44c74665b319646d1a2af25e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592352B2

Reaction notes

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