(Diethylamino)sulfur trifluoride → HCID 90203658, compound

HRID 1480204Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2(O)[CH2:11][O:10][CH2:9]2)=[CH:6][N:5]=[C:4]([C:13]#[N:14])[CH:3]=1.CCN(S(F)(F)[F:21])CC>ClCCl>[Cl:1][C:2]1[C:7]([C:8]2([F:21])[CH2:11][O:10][CH2:9]2)=[CH:6][N:5]=[C:4]([C:13]#[N:14])[CH:3]=1

Participants

Conditions

Temperature: -75 °C

Procedure

To a solution of 4-chloro-5-(3-hydroxyoxetan-3-yl)pyridine-2-carbonitrile (example 123b, 2.0 g, 9.5 mmol) in dry dichloromethane (50 ml) under an argon atmosphere cooled down to −75° C. was added DAST (1.61 g, 1.32 ml, 9.97 mmol). The reaction was stirred at −75° C. for 15 min, then let to warm up to 0° C. and stirred at 0° C. for 1 hour. The reaction was then quenched by addition of a 2M aqueous solution of sodium carbonate. The bi-phasic mixture was stirred at room temperature for 15 minutes, poured into a separatory funnel and extraction was carried out. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (1.81 g, 90%). MS (ESI, m/z): 213.0 (M+H+).

Workup

temperatureto warm up to 0° C.
stirringstirred at 0° C. for 1 hour
customThe reaction was then quenched by addition of a 2M aqueous solution of sodium carbonate
stirringThe bi-phasic mixture was stirred at room temperature for 15 minutes
additionpoured into a separatory funnel
extractionextraction
dry with materialThe organic phase was dried over sodium sulfate
customevaporated down to dryness
customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record: ord-2f9f600c43674b1a9a2aff50cc8f3e9e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Reaction notes

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