3,4-Difluorobenzeneboronic acid → HCID 23654205, compound

HRID 1785514Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]=[CH:11]2)=[N:7][C:6]=1Br)=[O:4].[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[F:31]>>[F:24][C:25]1[CH:26]=[C:27]([C:6]2[N:7]=[C:8]([N:10]3[C:14]4[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=4[N:12]=[CH:11]3)[S:9][C:5]=2[C:3]([OH:2])=[O:4])[CH:28]=[CH:29][C:30]=1[F:31]

Participants

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acid

HCID 57595851HCID 57595851, compound

Product 1

HCID 23654205HCID 23654205, compoundYield 21%

Procedure

In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3,4-difluorophenylboronic acid (23.7 mg, 0.15 mmol) gave 4-(3,4-Difluoro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (8.7 mg, 21%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (s, 1 H); 8.22-8.32 (m, 1 H); 7.88-8.00 (m, 1 H); 7.80 (s, 1 H); 7.55 (dt, 1 H); 7.39 (s, 1 H); 3.88 (s, 3 H), 3.85 (s, 3 H). MS 418 m/z (M+1 ).

Sources & evidence

ORD record: ord-38f139cc1fb6484eb8bbcda09d1148c6
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504513B2

Reaction notes

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