2-Methoxypyrimidine-5-boronic acid → HCID 178524143, compound

HRID 1519337Notes

Reaction equation

HRID 1519337 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[O:26][C:27]1[N:32]=[CH:31][C:30](B(O)O)=[CH:29][N:28]=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:30]4[CH:29]=[N:28][C:27]([OH:26])=[N:32][CH:31]=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 27367782-Methoxypyrimidine-5-boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 178524143HCID 178524143, compoundYield 76.5%

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-methoxypyrimidine-5-boronic acid (available from Combi-Blocks Inc.; 77 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-hydroxy-pyrimidin-5-yl)-benzoic acid (85 mg, 76%). 1H NMR (400 MHz, DMSO-d6) δ 13.40 (br s, 1H), 8.42-8.62 (m, 2H), 8.20-8.38 (m, 2H), 8.04-8.14 (m, 1H), 7.76 (d, J=8.3 Hz, 2H), 7.61 (d, J=7.5 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-7da7098797b743fe9a3d87dd59d0fbb7
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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