Methyl chloroacetate → 2-(Chloromethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyridine

HRID 1771985Notes

Reaction equation

[NH2:1][N:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]1=[NH2+:9].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[Cl:23][CH2:24][C:25](OC)=O.C(=O)([O-])[O-].[K+].[K+]>CCO>[Cl:23][CH2:24][C:25]1[N:9]=[C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[N:2]2[N:1]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1-amino-6-methylpyridin-2(1H)-iminium-2,4,6-trimethylbenzenesulfonate (520 mg, crude product from the previous step, 1.61 mmol), methyl 2-chloroacetate (700 mg, 7.80 mmol) and potassium carbonate (444 mg, 3.22 mmol) in EtOH (10 m L) was stirred at 80° C. for 16 h. After cooled to room temperature, the reaction mixture was concentrated and purified by silica gel column chromatography (eluting with EtOAc in PE, a gradient from 17% to 30% v/v) to give the title compound (290 mg, yield 84%). ESI MS: m/z 182, 184 [M+H]+.

Workup

temperatureAfter cooled to room temperature
concentrationthe reaction mixture was concentrated
custompurified by silica gel column chromatography (
washeluting with EtOAc in PE

Sources & evidence

ORD record: ord-e8e447ff2804498ea4a79d0ad673a76f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249162B2

Reaction notes

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