Methyl 5-bromo-6-chloronicotinate → 5-Bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

HRID 332273Notes

Reaction equation

HRID 332273 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].[Br:15][C:16]1[C:17](Cl)=[N:18][CH:19]=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22]>>[CH3:24][O:23][C:21](=[O:22])[C:20]1[CH:25]=[C:16]([Br:15])[C:17]([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:18][CH:19]=1

Participants

3

Reactant 2

HCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 684448555-Bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl esterYield 37%

Procedure

As described for example 5, (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (3.60 mg, 19.0 mmol) was converted using methyl 5-bromo-6-chloronicotinate instead of 6-chloronicotinonitrile to the title compound (SiO2, heptane:ethyl acetate=90:10 to 60:40, 2.83 g, 37%) which was obtained as a white solid. MS: m/e=403.3/405.2 [M+H]′.

Sources & evidence

ORD record
ord-0194a74e579249d0bda8440fdbd32b96
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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