3-Pyridinylboronic acid → HCID 86679850, compound

HRID 1519354Notes

Reaction equation

HRID 1519354 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.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=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:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=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 27343783-Pyridinylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679850HCID 86679850, compoundYield 14%

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 pyridine-3-boronic acid (available from Combi-Blocks Inc.; 49 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-pyridin-3-yl-benzoic acid (12 mg, 14%). 1H NMR (300 MHz, DMSO-d6), δ 13.27 (br s, 1H), 8.56-8.63 (m, 2H), 8.45-8.51 (m, 2H), 8.34 (d, J=1.9 Hz, 1H), 8.28 (dd, J=7.9, 1.9 Hz, 1H), 8.10 (dd, J=8.5, 2.1 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.48 (dd, J=7.7, 5.1 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-8c98a71672e84b3cb86292db4e4ed7bf
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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