(2-Methylpyridin-3-yl)boronic acid--hydrogen chloride (1/1) → HCID 71535816, compound

HRID 1519351Notes

Reaction equation

HRID 1519351 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.Cl.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[C:27]=1[CH3:35]>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:28]4[C:27]([CH3:35])=[N:26][CH:31]=[CH:30][CH:29]=4)=[C:4]([CH:9]=3)[C:3]([OH:2])=[O:24])[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 44119808(2-Methylpyridin-3-yl)boronic acid--hydrogen chloride (1/1)HCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 71535816HCID 71535816, compoundYield 59%

Procedure

Using the conditions of General Procedure C 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; 111 mg, 0.25 mmol) was reacted with 2-picoline-3-boronic acid hydrochloride salt (available from Combi-Blocks Inc.; 87 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2-(2-methyl-pyridin-3-yl)-benzoic acid (65 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ 8.56 (d, J=1.8 Hz, 1H), 8.49 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.30 (dd, J=7.9, 1.9 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.21-7.30 (m, 1H), 2.08 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-75be6f3b23294e93b982b4e9c83820ed
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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