5-Chloro-2-nitrophenylboronic acid → 5'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acid

HRID 1519270Notes

Reaction equation

HRID 1519270 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.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([N+:35]([O-:37])=[O:36])=[C:30](B(O)O)[CH:31]=1>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N+:35]([O-:37])=[O:36])=[C:28]([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:27]=1

Participants

3

Reactant 2

HCID 102144605-Chloro-2-nitrophenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 715388795'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2'-nitro-biphenyl-2-carboxylic acidYield 7%

Procedure

5′-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid was prepared in 7% yield (for two steps) from 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6) and 5-chloro-2-nitrophenylboronic acid (available from Combi-Blocks Inc.) using General Procedure A for Suzuki Coupling and Hydrolysis in Parallel Mode. 1H NMR (300 MHz, DMSO-d6) δ 13.29 (br s, 1H), 8.60 (d, J=1.9 Hz, 1H), 8.50 (s, 1H), 8.29-8.37 (m, 2H), 8.20 (d, J=8.9 Hz, 2H), 8.10 (dd, J=8.4, 2.0 Hz, 1H), 7.73-7.82 (m, 2H), 7.60 (d, J=2.3 Hz, 1H), 7.53 (d, J=7.9 Hz, 1H).

Workup

  1. customfor Suzuki Coupling and Hydrolysis in Parallel Mode

Sources & evidence

ORD record
ord-0444e300c5094ee498a215fef0411f90
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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