[4-(Propan-2-yl)pyrimidin-5-yl]boronic acid → HCID 71535815, compound

HRID 1519349Notes

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.[CH:25]([C:28]1[C:33](B(O)O)=[CH:32][N:31]=[CH:30][N:29]=1)([CH3:27])[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:33]4[C:28]([CH:25]([CH3:27])[CH3:26])=[N:29][CH:30]=[N:31][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

Reactant 2

HCID 44119845[4-(Propan-2-yl)pyrimidin-5-yl]boronic acid

HCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 71535815HCID 71535815, compoundYield 14.9%

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 4-isopropylpyrimidine-5-boronic acid (available from Combi-Blocks Inc.; 66 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-(4-isopropyl-pyrimidin-5-yl)-benzoic acid (14 mg, 14%). 1H NMR (300 MHz, DMSO-d6) δ 13.30 (br s, 1H), 9.14 (s, 1H), 8.62 (d, J=1.7 Hz, 1H), 8.50 (d, J=2.4 Hz, 2H), 8.29-8.36 (m, 2H), 8.10 (dd, J=8.4, 2.0 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.55 (d, J=8.1 Hz, 5H), 2.75-2.85 (m, 1H), 1.03-1.19 (m, 6H).

Workup

customthe acid was purified

Sources & evidence

ORD record: ord-ebd82e487f264c5593a4b0692e85815f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073881B2

Reaction notes

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