(Diethylamino)sulfur trifluoride → 2-Chloro-3-(3-fluorooxetan-3-yl)-6-methylpyridine

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2(O)[CH2:11][O:10][CH2:9]2)=[CH:6][CH:5]=[C:4]([CH3:13])[N:3]=1.C(N(S(F)(F)[F:20])CC)C>>[Cl:1][C:2]1[C:7]([C:8]2([F:20])[CH2:11][O:10][CH2:9]2)=[CH:6][CH:5]=[C:4]([CH3:13])[N:3]=1

Participants

Reactant 2

HCID 123472(Diethylamino)sulfur trifluoride

HCID 902026243-(2-Chloro-6-methylpyridin-3-yl)oxetan-3-ol

Product 1

HCID 902026462-Chloro-3-(3-fluorooxetan-3-yl)-6-methylpyridineYield 56%

Procedure

In analogy to the procedure described in Example 130 b), 3-(2-chloro-6-methylpyridin-3-yl)oxetan-3-ol (Example 134 a, 1.5 g, 7.51 mmol) was reacted with diethylaminosulfur trifluoride to obtain the title compound (850 mg, 56%) as colorless liquid, MS (ESI): m/e=202.1 [MH+].

Sources & evidence

ORD record: ord-d417c9c2bcfc4bd7a56a699dfc14af04
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303012B2

Reaction notes

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