2-Ethoxypyrimidine-5-boronic acid → 5-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2-(2-ethoxy-pyrimidin-5-yl)-benzoic acid

HRID 1519335Notes

Reaction equation

HRID 1519335 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.[CH2:25]([O:27][C:28]1[N:33]=[CH:32][C:31](B(O)O)=[CH:30][N:29]=1)[CH3:26]>>[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:31]4[CH:30]=[N:29][C:28]([O:27][CH2:25][CH3:26])=[N:33][CH:32]=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 164271422-Ethoxypyrimidine-5-boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 715352535-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2-(2-ethoxy-pyrimidin-5-yl)-benzoic acidYield 3%

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-ethoxypyrimidine-5-boronic acid (available from Combi-Blocks Inc.; 84 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-ethoxy-pyrimidin-5-yl)-benzoic acid (3 mg, 3%). LCMS analysis indicated that the material was ˜69% pure, as measured by UV at 214 nm. LRMS m/z 471.8 (M+H+).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-056f72b0e40247059c6b9b7039083d2c
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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