(3-Methylpyridin-4-yl)boronic acid--hydrogen chloride (1/1) → HCID 71535817, compound

HRID 1519352Notes

Reaction equation

HRID 1519352 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][C:29](B(O)O)=[C:28]([CH3:35])[CH:27]=1>>[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:29]4[CH:30]=[CH:31][N:26]=[CH:27][C:28]=4[CH3:35])=[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 46739017(3-Methylpyridin-4-yl)boronic acid--hydrogen chloride (1/1)HCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 71535817HCID 71535817, compoundYield 42%

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 3-picoline-4-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-(3-methyl-pyridin-4-yl)-benzoic acid (46 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ 13.30 (br s, 1H), 8.59-8.66 (m, 2H), 8.50 (s, 1H), 8.30-8.38 (m, 2H), 8.10 (dd, J=8.5, 1.9 Hz, 1H), 7.88-7.94 (m, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.56-7.63 (m, 1H), 7.52 (d, J=8.1 Hz, 1H), 2.34 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-eaff41a660fb49a98c3f01b7821d3256
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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