Water → HCID 86082307, compound

HRID 1035010Notes

Reaction equation

HRID 1035010 reaction equation
Cl[C:2]1[N:9]=[C:8]([Cl:10])[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15].[H-].[Na+].O>CN(C)C=O>[Cl:10][C:8]1[C:7]([F:11])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:15][CH2:14][C:13]([F:17])([F:16])[F:12])[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrile

Product 1

HCID 86082307HCID 86082307, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,6-dichloro-5-fluoro-nicotinonitrile (900 mg, 5.7 mmol), 2,2,2-trifluoro-ethanol (570 mg, 5.7 mmol), and NaH (60%) (273 mg, 6.8 mmol) in N,N-dimethylformamide (15 mL) was heated at 120° C. overnight. The reaction mixture was poured into water, and extracted with ethyl acetate (2×). The solvent was removed to give the title compound (1100 mg, 76%). MS (DCI/NH3) m/z 255 (M)+, 257 (M+2)+.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-adc8f02f252b438fabfd9c04ffe94645
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Reaction notes

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