Thionyl Chloride → 2-(4-Chloromethyl-5-methyl-isoxazol-3-yl)-5-fluoro-pyridine

HRID 1923520Notes

Reaction equation

HRID 1923520 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13]O)=[C:11]([CH3:15])[O:10][N:9]=2)=[N:6][CH:7]=1.S(Cl)([Cl:18])=O>C(Cl)Cl>[Cl:18][CH2:13][C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=2)=[N:9][O:10][C:11]=1[CH3:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66599256[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol

Product 1

HCID 666435292-(4-Chloromethyl-5-methyl-isoxazol-3-yl)-5-fluoro-pyridineYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol (1.0 g, 4.8 mmol) in DCM (9.6 mL) at 0° C. was added thionyl chloride (697 μL, 9.6 mmol) and the resulting mixture stirred for 30 min and then evaporated. After 1 h the reaction mixture was concentrated to give the title compound (1.07 g, 98%) as an off white solid. MS: m/e=227.2 [M+H]+.

Workup

  1. customevaporated
  2. concentrationAfter 1 h the reaction mixture was concentrated

Sources & evidence

ORD record
ord-6cd60dec73b1454399acefbadd5525bd
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

Loading…