1-Naphthaleneboronic acid → HCID 23654020, compound

HRID 1785503Notes

Reaction equation

HRID 1785503 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].[C:24]1(B(O)O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>>[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:32]4[C:33]5[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:29]=[CH:30][CH:31]=4)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 57595851HCID 57595851, compound

Product 1

HCID 23654020HCID 23654020, compoundYield 37%

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 1-naphthaleneboronic acid (25.8 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-naphthalen-1-yl-thiazole-5-carboxylic acid (15.9 mg, 37%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.41 (br.s., 1 H); 8.85 (s, 1 H); 8.01-8.09 (m, 2H); 7.92 (dd, 1 H); 7.72 (dd, 1 H); 7.69 (s, 1H); 7.50-7.65 (m, 3H); 7.40 (s, 1 H); 3.84 (s, 3 H); 3.68 (s, 3 H). MS m/z 432 (M+1).

Sources & evidence

ORD record
ord-3443172873194b13957611ed3d24b997
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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