(2-Acetylthiophen-3-yl)boronic acid → HCID 86679861, compound

HRID 1519368Notes

Reaction equation

HRID 1519368 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)[CH:7]=[CH:6][C:5]=1Br.[C:25]([C:28]1[S:29][CH:30]=[CH:31][C:32]=1B(O)O)(=[O:27])[CH3:26]>>[C:25]([C:28]1[S:29][CH:30]=[CH:31][C:32]=1[C:5]1[CH:6]=[CH:7][C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)=[CH:9][C:4]=1[C:3]([OH:2])=[O:24])(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 46739719(2-Acetylthiophen-3-yl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679861HCID 86679861, compoundYield 20%

Procedure

Using the conditions of General Procedure B for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 89 mg, 0.2 mmol) was reacted with 2-acetyl-3-thienylboronic acid (available from Aldrich Chemical Company, Inc.; 68 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2-(2-acetyl-thiophen-3-yl)-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid (19 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ 13.12 (br s, 1H), 8.52 (d, J=1.8 Hz, 1H), 8.49 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.25 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.94 (d, J=5.0 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.10 (d, J=5.0 Hz, 1H), 2.08 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-42875081c2f34f61adedf0c513e10b1b
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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