Cesium carbonate → (S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylate

HRID 1958154Notes

Reaction equation

HRID 1958154 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](Br)=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[F:25][C:26]([F:31])([F:30])[C@@H:27]([OH:29])[CH3:28]>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:29][C@@H:27]([CH3:28])[C:26]([F:31])([F:30])[F:25])=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6999971(2S)-1,1,1-Trifluoropropan-2-olHCID 86619571Methyl 5-bromo-6-(4-chlorophenyl)pyrazine-2-carboxylate

Product 1

HCID 66678867(S)-methyl 6-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrazine-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Bromo-6-(4-chlorophenyl)-2-pyrazinecarboxylic acid methyl ester (CAN 960247-79-4, 2.420 g, 7.39 mmol) was dissolved in dry DMSO (25 mL). Cesium carbonate (4.41 g, 8.13 mmol) and (S)-1,1,1-trifluoropropan-2-ol (927 mg, 8.13 mmol) were added and the reaction mixture was stirred at room temperature for 2 h. The mixture was partitioned between water and ethyl acetate; the organic phase was dried with MgSO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 100 g, 10% to 50% ethyl acetate in heptane) to yield 2.53 g (95%) of the title compound as yellow oil; MS (EI) 361.1 (M+H)+.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. dry with materialthe organic phase was dried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by flash chromatography (silica gel, 100 g, 10% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-3123d76dca42483dabb54e425ae3ea50
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

Loading…