4-Nitrophenylboronic acid → HCID 71538882, compound

HRID 1519302Notes

Reaction equation

HRID 1519302 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]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)([O-:27])=[O:26]>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:9]=[C:4]([C:3]([OH:2])=[O:24])[C:5]([C:31]4[CH:32]=[CH:33][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=4)=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 27735524-Nitrophenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 71538882HCID 71538882, compoundYield 18%

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-nitrophenylboronic acid (available from Combi-Blocks Inc.; 67 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-4′-nitro-biphenyl-2-carboxylic acid (17 mg, 18%). 1H NMR (400 MHz, DMSO-d6) δ 13.35 (br s, 3H), 8.50 (s, 1H) 8.47 (s, 1H), 8.34 (s, 1H), 8.27-8.32 (m, 2H), 8.10 (d, J=8.5 Hz, 1H), 7.77 (d, J=6.8 Hz, 1H), 7.68 (d, J=7.0 Hz, 2H), 7.61 (d, J=6.5 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-d440c7e083824f0698f93d26866707c6
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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