(3-Ethoxycarbonylphenyl)boronic acid → HCID 67420648, compound

HRID 2219371Notes

Reaction equation

HRID 2219371 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:8][O:9][C:10]=2[CH3:11])[N:3]=[CH:2]1.[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22])[CH3:19]>>[CH2:18]([O:20][C:21](=[O:22])[C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([N:1]2[CH:5]=[C:4]([C:6]3[C:7]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[N:8][O:9][C:10]=3[CH3:11])[N:3]=[CH:2]2)[CH:28]=1)[CH3:19]

Participants

3

Reactant 2

HCID 3249312(3-Ethoxycarbonylphenyl)boronic acidHCID 178434980HCID 178434980, compound

Product 1

HCID 67420648HCID 67420648, compoundYield 52%

Procedure

As described for Example 3, 4-(1H-imidazol-4-yl)-5-methyl-3-phenyl-isoxazole (2.25 g, 10.0 mmol) was converted, using 3-ethoxycarbonylphenylboronic acid (2.89 g, 15 mmol), instead of 4-fluorophenylboronic acid, which after purification by chromatography (SiO2, heptane:ethyl acetate=50:50) afforded the title compound (1.9 g, 52%) which was obtained as a light yellow solid. MS: m/e=374.1[M+H]+.

Workup

  1. custominstead of 4-fluorophenylboronic acid, which after purification by chromatography (SiO2, heptane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-c71201d4c13f4cbc8b32cc01f70d0d10
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

Loading…