2-Methoxypyrimidine-5-boronic acid → HCID 71535254, compound

HRID 1519336Notes

Reaction equation

HRID 1519336 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.[CH3:25][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]([O:26][CH3:25])=[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 71535254HCID 71535254, compoundYield 1%

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 and 2-methoxypyrimidine-5-boronic acid (available from Combi-Blocks Inc.; 62 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2-(2-methoxy-pyrimidin-5-yl)-benzoic acid (0.9 mg, 1%). LCMS analysis indicated that the material was ˜100% pure, as measured by UV at 214 nm. LRMS m/z 457.8 and 459.8 (M+H+).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-48a355da611e42f8aee6ef6655af5a1c
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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