2-Methylphenyl boronic acid → HCID 86679879, compound

HRID 1519389Notes

Reaction equation

HRID 1519389 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.[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O>>[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:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[CH3:25])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679879HCID 86679879, compoundYield 72%

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 2-methylphenylboronic acid (available from Combi-Blocks Inc.; 54 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]-2′-methyl-biphenyl-2-carboxylic acid (63 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ 12.92 (br s, 1H), 8.46 (d, J=4.8 Hz, 2H), 8.34 (s, 1H), 8.22 (d, J=8.0 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.17-7.32 (m, 3H), 7.09 (d, J=7.0 Hz, 1H), 2.08 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-9e3a1de0ce97442694fd2b7689aa2a8f
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

Loading…