Methanol → 3-{6-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridin-3-yl}-oxetan-3-ol

HRID 332335Notes

Reaction equation

HRID 332335 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[N:6][CH:7]=1.C([Li])CCC.[O:28]1[CH2:31][C:30](=[O:32])[CH2:29]1.CO>C1COCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]2[C:10]([CH2:9][O:8][C:5]3[N:6]=[CH:7][C:2]([C:30]4([OH:32])[CH2:31][O:28][CH2:29]4)=[CH:3][CH:4]=3)=[C:14]([CH3:15])[O:13][N:12]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 150242543-OxetanoneHCID 684428165-Bromo-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridineHCID 178418339Butyllithium

Product 1

HCID 575202683-{6-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridin-3-yl}-oxetan-3-olYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridine (110 mg, 0.3 mmol) in THF (3 mL) was treated at −78° C. with n-butyllithium (1.6 M solution in hexanes, 189 μL, 0.3 mmol) and then with 3-oxetanone (23.0 mg, 0.3 mmol). After 20 minutes methanol was added and the mixture was warmed to room temperature. Concentration and purification by chromatography (silicagel, heptane:ethyl acetate=85:15 to 8:3) to afforded the title product (32 mg, 30%) which was obtained as a colourless oil. MS: m/e=357.1 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (silicagel, heptane:ethyl acetate=85:15 to 8:3)

Sources & evidence

ORD record
ord-1cb792b7f00c404f8733c73f9ddd809f
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

Loading…