(2-Aminocarbonylphenyl)boronic acid → 2'-Carbamoyl-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid

HRID 1519334Notes

Reaction equation

HRID 1519334 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.[NH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O)=[O:27]>>[C:26]([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])[NH2:25]

Participants

3

Reactant 2

HCID 2737809(2-Aminocarbonylphenyl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 715352522'-Carbamoyl-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acidYield 16%

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-aminocarbonylphenylboronic acid (available from Combi-Blocks Inc.; 66 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-carbamoyl-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (15 mg, 8%). 1H NMR (300 MHz, DMSO-d6) δ 13.07 (br s, 1H), 8.46 (s, 1H), 8.36 (d, J=14.1 Hz, 2H), 8.04-8.18 (m, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.58 (d, J=7.2 Hz, 2H), 7.42-7.51 (m, 2H), 7.12-7.34 (m, 3H). The compound of Example 81 has the same formula as the compound of Example 113.

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-a80001f193264d079bc5b59e62f223af
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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