2-Acetylphenylboronic acid → HCID 86679859, compound

HRID 1519366Notes

Reaction equation

HRID 1519366 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[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O)(=[O:27])[CH3:26]>>[C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:5]1[C:4]([C:3]([OH:2])=[O:24])=[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]=1)(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 27343092-Acetylphenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679859HCID 86679859, compoundYield 15%

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-acetylphenylboronic acid (available from ASDI Incorporated; 66 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-acetyl-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (14 mg, 15%). 1H NMR (400 MHz, DMSO-d6) δ 12.97 (br s, 1H), 8.44-8.50 (m, 2H), 8.34 (d, J=1.8 Hz, 1H), 8.20 (dd, J=7.9, 1.9 Hz, 1H), 8.09 (dd, J=8.3, 2.0 Hz, 1H), 7.81-7.88 (m, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.55-7.64 (m, 1H), 7.45-7.54 (m, 1H), 7.34 (d, J=8.0 Hz, 1H), 7.19-7.28 (m, 1H), 6.52 (s, 1H), 2.32 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-530a9163eb8e4cdd96c731044b4cdb63
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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