Cesium carbonate → HCID 67095583, compound

HRID 909103Notes

Reaction equation

HRID 909103 reaction equation
[Cl:1][C:2]1[C:3]([F:37])=[C:4]([CH:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][N:9]2[C:28]([C:30]2[CH:35]=[CH:34][C:33](=[O:36])[NH:32][CH:31]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.[C:38](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.IC.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:37])=[C:4]([CH:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:11]([CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:10][N:9]2[C:28]([C:30]2[CH:35]=[CH:34][C:33](=[O:36])[N:32]([CH3:38])[CH:31]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 10796Cesium carbonateHCID 67095582HCID 67095582, compound

Product 1

HCID 67095583HCID 67095583, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-1-(6-oxo-1,6-dihydro-pyridine-3-carbonyl)-pyrrolidine-3-carbonitrile (15.1 mg, 0.0277 mmol, example 40), cesium carbonate (27 mg, 0.0829 mmol, Aldrich) in DMF (3 mL) and iodomethane was stirred at room temp. for 3 hrs before it was diluted with EtOAc, washed with water and brine, dried and concentrated. The residue was purified by flash column to give rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-1-(1-methyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-pyrrolidine-3-carbonitrile (15.0 mg, 96%) as a white solid.

Workup

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-2ba2d59756c141f6a8f9c5312aacfb04
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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