Cesium carbonate → HCID 57809940, compound

HRID 2106011Notes

Reaction equation

HRID 2106011 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:30])=[C:6]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH:14]=[CH:13]2)[CH:7]=1.Cl[C:32]([F:38])([F:37])C(OC)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[F:37][CH:32]([F:38])[O:30][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[C:8]([CH3:28])([CH3:29])[CH2:9][C:10]([OH:27])([C:23]([F:25])([F:26])[F:24])[CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH:14]=[CH:13]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 73935Methyl chlorodifluoroacetateHCID 16099240HCID 16099240, compound

Product 1

HCID 57809940HCID 57809940, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (0.05 g), methyl 2-chloro-2,2-difluoroacetate (0.014 mL) and cesium carbonate (0.195 g) in 1.5 mL of DMF was heated at 60° C. for 20 hours, cooled to room temperature, diluted with ethyl acetate, and washed with aqueous acetic acid, water, and brine. The residue was purified by reverse-phase HPLC using acetonitrile/water as the eluent. The product rich fractions were concentrated in vacuo and provided 1-[4-(2-difluoromethoxy-5-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one, m.p. 150° C.-155° C.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with aqueous acetic acid, water, and brine
  3. customThe residue was purified by reverse-phase
  4. concentrationThe product rich fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-68b83c842e71404698ebc297d72d14dc
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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