Thionyl Chloride → 3-(Azidomethyl)-2-chloro-5-fluoropyridine

HRID 2240379Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][C:5]([F:10])=[CH:4][N:3]=1.S(Cl)(Cl)=O.[N-:15]=[N+:16]=[N-:17].[Na+]>>[N:15]([CH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([F:10])[CH:6]=1)=[N+:16]=[N-:17]

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 33557Sodium Azide

HCID 24229204(2-Chloro-5-fluoropyridin-3-yl)methanol

Product 1

HCID 860822623-(Azidomethyl)-2-chloro-5-fluoropyridine

Procedure

(2-chloro-5-fluoro-pyridin-3-yl)-methanol, thionyl chloride and sodium azide were processed according to the method of Example 115A to provide the product. MS (ESI+) m/z 187 (M+H)+.

Workup

customto provide the product

Sources & evidence

ORD record: ord-aa528c46428945b28dfa0667270d03a1
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723367B2

Reaction notes

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