(6-Cyanopyridin-2-yl)boronic acid → HCID 86679853, compound

HRID 1519357Notes

Reaction equation

HRID 1519357 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[N:32]=[C:31](B(O)O)[CH:30]=[CH:29][CH:28]=1)#[N:26]>>[C:25]([C:27]1[N:32]=[C:31]([C:5]2[CH:6]=[CH:7][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:9][C:4]=2[C:3]([OH:2])=[O:24])[CH:30]=[CH:29][CH:28]=1)#[N:26]

Participants

3

Reactant 2

HCID 17750495(6-Cyanopyridin-2-yl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679853HCID 86679853, compoundYield 16%

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 6-cyanopyridine-2-boronic acid (available from CombiPhos Catalysts, Inc.; 59 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2-(6-cyano-pyridin-2-yl)-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid (14 mg, 16%). 1H NMR (300 MHz, DMSO-d6) δ 13.14 (br s, 1H), 8.50 (s, 1H), 8.40 (s, 1H), 8.35 (s, 1H), 8.24-8.32 (m, 1H), 8.00-8.16 (m, 3H), 7.73-7.88 (m, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-8112beffcafc4828b86bc48d0c8a0c6e
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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