Iodoethane → HCID 57809834, compound

HRID 2106010Notes

Reaction equation

HRID 2106010 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.I[CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:32]([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)[CH3:33]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 16099240HCID 16099240, compound

Product 1

HCID 57809834HCID 57809834, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (0.053 g), iodoethane (0.011 mL) and powdered potassium carbonate (0.090 g) in 1 mL of anhydrous DMF was heated at 80° C. for 18 hours, cooled to room temperature, and diluted with water and filtered. The solid was purified with flash silica gel chromatography using ethyl acetate as the eluent. The product rich fraction were concentrated in vacuo and provided 1-[4-(2-ethoxy-5-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one, m.p. 195° C.-196° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe solid was purified with flash silica gel chromatography
  4. concentrationThe product rich fraction were concentrated in vacuo

Sources & evidence

ORD record
ord-7c7e64e050594428a2d4fb6a6484a25e
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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