Water → 2-(Azidomethyl)-6-(2,2,2-trifluoroethoxy)pyridine

HRID 715379Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:4]=1.[N-:15]=[N+:16]=[N-:17].[Na+].O>CC(N(C)C)=O>[N:15]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:4]=1)=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridine (0.35 g, 1.55 mmol, Step-4) and sodium azide (0.20 g, 3.10 mmol) in DMA (8 mL) is stirred 90° C. for 1 hour. The reaction mixture is poured into water (50 mL), and extracted with n-hexane/EtOAc (1:10, 50 mL). The organic layer is washed with water (50 mL) and dried over sodium sulfate. After filtration, the organic fraction is concentrated in vacuo to give 0.44 g (>99% yield) of the title compound as colorless oil. This material is used for the next reaction (Step-6) without further purification.

Workup

extractionextracted with n-hexane/EtOAc (1:10, 50 mL)
washThe organic layer is washed with water (50 mL)
dry with materialdried over sodium sulfate
filtrationAfter filtration
concentrationthe organic fraction is concentrated in vacuo

Sources & evidence

ORD record: ord-4f010b17005c4f21bd2255fe74833640
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187475B2

Reaction notes

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