4-Cyanophenylboronic acid → HCID 71535819, compound

HRID 1519359Notes

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:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)#[N:26]>>[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:5]2[C:4]([C:3]([OH:2])=[O:24])=[CH:9][C:8]([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=4)[N:14]=3)=[CH:7][CH:6]=2)=[CH:29][CH:28]=1)#[N:26]

Participants

Reactant 2

HCID 27343264-Cyanophenylboronic acid

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

Product 1

HCID 71535819HCID 71535819, compoundYield 22.2%

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 4-cyanophenylboronic acid (available from Combi-Blocks Inc.; 59 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4′-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (20 mg, 22%). 1H NMR (400 MHz, DMSO-d6) δ 13.31 (br s, 1H), 8.49 (s, 1H), 8.43 (d, J=1.8 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.26 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.4, 2.1 Hz, 1H), 7.92 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.56-7.64 (m, 3H).

Workup

customthe acid was purified

Sources & evidence

ORD record: ord-7de19d958d524ad9b8c24deb0c78753d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073881B2

Reaction notes

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