Cesium carbonate → HCID 59682253, compound

HRID 1394413Notes

Reaction equation

HRID 1394413 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]3[C:17](=[O:28])[N:18]([CH3:27])[C:19]4[C:24]([C:25]=3[OH:26])=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:36]([F:42])([F:41])C(OC)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]3[C:17](=[O:28])[N:18]([CH3:27])[C:19]4[C:24]([C:25]=3[O:26][CH:36]([F:42])[F:41])=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 73935Methyl chlorodifluoroacetateHCID 54707817HCID 54707817, compound

Product 1

HCID 59682253HCID 59682253, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of example 145, Cs2CO3 (2 eq) in DMF (0.2M) was heated at 100° C. (open flask) then methyl chlorodifluoroacetate (2 eq) was added and the mixture stirred at 90-110° C. for 3 h. After cooling to rt, the mixture was diluted with water, extracted with ethyl acetate and the solvent evaporated. The residue was purified by crystallisation in hexane\ether to give the title compound as a white powder.

Workup

  1. temperatureAfter cooling to rt
  2. extractionextracted with ethyl acetate
  3. customthe solvent evaporated
  4. customThe residue was purified by crystallisation in hexane\ether

Sources & evidence

ORD record
ord-29b088f30d7843d387065f42031b8c24
Source dataset
uspto-grants-2008_03
Patent number
US07348433B2

Reaction notes

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