2-Formylphenylboronic acid → HCID 86679864, compound

HRID 1519371Notes

Reaction equation

HRID 1519371 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.[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)=[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:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[CH:25]=[O:26])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 2921892-Formylphenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679864HCID 86679864, compoundYield 49.5%

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-formylphenylboronic acid (available from Frontier Scientific, Inc.; 60 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′-formyl-biphenyl-2-carboxylic acid (45 mg, 49%). 1H NMR (400 MHz, DMSO-d6) δ 13.11 (br s, 1H), 9.80 (br s, 1H), 8.54 (s, 1H), 8.49 (s, 1H), 8.34 (s, 1H), 8.27 (d, J=7.8 Hz, 1H), 8.10 (d, J=8.5 Hz, 1H), 7.93 (d, J=7.5 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.73 (t, J=7.2 Hz, 1H), 7.61 (t, J=7.3 Hz, 1H), 7.51 (d, J=7.8 Hz, 1H), 7.36 (d, J=7.5 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-7d5df02b5922410599b601f141039fd5
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

Loading…