Cesium carbonate → HCID 71285673, compound

HRID 536534Notes

Reaction equation

HRID 536534 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]([F:12])([F:11])[CH2:9]I.[F:13][C:14]1[CH:42]=[CH:41][CH:40]=[CH:39][C:15]=1[CH2:16][N:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[C:19]([C:26]2[N:27]=[C:28]([OH:38])[C:29]3[C:34]([CH3:36])([CH3:35])[C:33](=[O:37])[NH:32][C:30]=3[N:31]=2)=[N:18]1>CN(C=O)C>[F:13][C:14]1[CH:42]=[CH:41][CH:40]=[CH:39][C:15]=1[CH2:16][N:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[C:19]([C:26]2[N:27]=[C:28]([O:38][CH2:9][C:8]([F:12])([F:11])[F:7])[C:29]3[C:34]([CH3:36])([CH3:35])[C:33](=[O:37])[NH:32][C:30]=3[N:31]=2)=[N:18]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 178429272HCID 178429272, compound

Product 1

HCID 71285673HCID 71285673, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

177 mg (0.54 mmol) of caesium carbonate and 114 mg (0.54 mmol) of 2,2,2-trifluoroethyl iodide were added to a suspension of 200 mg (0.5 mmol) of the compound from example 109 in DMF (1.97 ml) and it was stirred overnight at RT. Then it was heated in the microwave to 120° C. for 1 h. The reaction mixture was purified by preparative HPLC (Chromatorex C18, gradient of acetonitrile/0.01% aq. formic acid). Yield: 14.5 mg (6% of theor.).

Workup

  1. temperatureThen it was heated in the microwave to 120° C. for 1 h
  2. customThe reaction mixture was purified by preparative HPLC (Chromatorex C18, gradient of acetonitrile/0.01% aq. formic acid)

Sources & evidence

ORD record
ord-ee323363406f4c048fc3627be19aa918
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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