3-Isopropylbenzeneboronic acid → HCID 23653917, compound

HRID 1785497Notes

Reaction equation

HRID 1785497 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].[CH:24]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1)([CH3:26])[CH3:25]>>[CH3:20][O:19][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:14]2[N:10]([C:8]3[S:9][C:5]([C:3]([OH:2])=[O:4])=[C:6]([C:31]4[CH:30]=[CH:29][CH:28]=[C:27]([CH:24]([CH3:26])[CH3:25])[CH:32]=4)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 27734783-Isopropylbenzeneboronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23653917HCID 23653917, compoundYield 44%

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-isopropylphenylboronic acid (24.6 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-isopropyl-phenyl)-thiazole-5-carboxylic acid (18.6 mg, 44%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.61 (br.s., 1 H); 8.83 (s, 1 H); 7.88 (s, 1 H); 7.83 (t, 1 H); 7.74 (dt, 1 H); 7.39 (s, 1 H); 7.40 (t, 1 H); 7.36 (dt, 1 H); 3.86 (s, 3 H); 3.85 (s, 3 H); 2.93-3.03 (m, 1 H); 1.26 (d, 6 H). MS m/z 424 (M+1 ).

Sources & evidence

ORD record
ord-3a8fbc60df854bfdaf019653858ba679
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

Loading…