2,2,2-Trifluoroethanol → HCID 24800611, compound

HRID 1159260Notes

Reaction equation

HRID 1159260 reaction equation
[CH:1]1([C@:4]([OH:24])([CH3:23])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12](Br)=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.[F:37][C:38]([F:42])([F:41])[CH2:39][OH:40]>>[CH:1]1([C@:4]([OH:24])([CH3:23])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12]([O:40][CH2:39][C:38]([F:42])([F:41])[F:37])=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 86616978HCID 86616978, compound

Product 1

HCID 24800611HCID 24800611, compoundYield 98%

Procedure

To a solution of 0.041 g (0.001 mol) 5-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((R)-2-cyclopropyl-2-hydroxy-propyl)-amide (example 62a) in 1.0 ml 2,2,2-trifluoroethanol was added 0.200 g (0.006 mol) cesium carbonate and the mixture was stirred at room temperature for 7 days. The reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=2:1 to yield 0.042 g (98% yield) of the title compound as white crystals melting at 96-97° C.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe phases were separated
  3. customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-f06a369a3d6340d9ad5d7d43168ec15c
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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