Thionyl Chloride → 5-(Chloromethyl)imidazo[1,5-a]pyridine

HRID 280230Notes

Reaction equation

[CH:1]([C:3]1[N:8]2[CH:9]=[N:10][CH:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1)=O.[BH4-].[Na+].OCC1N2C=NC=C2C=CC=1.S(Cl)([Cl:27])=O>>[Cl:27][CH2:1][C:3]1[N:8]2[CH:9]=[N:10][CH:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 24386Thionyl Chloride

HCID 4311764Sodium borohydride

HCID 13206163Imidazo[1,5-a]pyridine-5-carbaldehyde

HCID 23321868Imidazo[1,5-a]pyridin-5-ylmethanol

Product 1

HCID 233218555-(Chloromethyl)imidazo[1,5-a]pyridine

Procedure

5-Chloromethylimidazo[1,5-a]pyridine is prepared from 5-formylimidazo-[1,5-a]pyridine by reduction with sodium borohydride to 5-hydroxymethylimidazo[1,5-a]pyridine and subsequent treatment with thionyl chloride.

Sources & evidence

ORD record: ord-b350f305caaf474c99183e1491f8b558
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04588732

Reaction notes

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