(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol → 5-Bromo-2-methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid ethyl ester

HRID 331773Notes

Reaction equation

HRID 331773 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[CH2:15]([O:17][C:18](=[O:28])[C:19]1[CH:24]=[C:23]([Br:25])[C:22](O)=[N:21][C:20]=1[CH3:27])[CH3:16]>>[CH2:15]([O:17][C:18](=[O:28])[C:19]1[CH:24]=[C:23]([Br:25])[C:22]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:21][C:20]=1[CH3:27])[CH3:16]

Participants

3

Reactant 2

HCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 178468566HCID 178468566, compound

Product 1

HCID 684443615-Bromo-2-methyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid ethyl esterYield 76%

Procedure

As described for example 4, (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (402 mg, 2.12 mmol) was converted using 5-bromo-6-hydroxy-2-methyl-nicotinic acid ethyl ester instead of 2-hydroxy-5-trifluoromethylpyridine to the title compound (SiO2, heptane:ethyl acetate=100:0 to 50:50, 700 mg, 76%) which was obtained as a colourless oil. MS: m/e=431.1/433.2 [M+H]+.

Sources & evidence

ORD record
ord-c54653c2532444bfbecdfc6e37a4ef7d
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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