Methyl 4-fluorobenzoylacetate → HCID 19864531, compound

HRID 1199986Notes

Reaction equation

HRID 1199986 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[CH:4][CH:3]=1.[CH3:15][C:16]1[N:17]([CH2:25][CH2:26][CH2:27]CO)[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N:24]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:7])[CH2:8][C:9]([O:11][CH2:12][CH2:27][CH2:26][CH2:25][N:17]2[C:18]3[CH:23]=[CH:22][N:21]=[CH:20][C:19]=3[N:24]=[C:16]2[CH3:15])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 579425Methyl 4-fluorobenzoylacetateHCID 19864515HCID 19864515, compound

Product 1

HCID 19864531HCID 19864531, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methyl 4-fluorobenzoylacetate (0.78 g, 4 mM) and 4-(2-methylimidazo[4,5-c]pyrid-1-yl)butanol (0.82 g, 4 mM--see Preparation 16) were heated at reflux in toluene (100 cm3) allowing the toluene to reduce to about 20 cm3 over a period of 2 hours. The remaining toluene was removed in vacuo and the residue purified by column chromatography on silica (Merck "Kieselgel 60"--Trade Mark) eluting with dichloromethane:methanol 19:1. Evaporation of the appropriate fractions gave the title compound as a colourless oil, (1.05 g, 71%).

Workup

  1. customThe remaining toluene was removed in vacuo
  2. customthe residue purified by column chromatography on silica (Merck "Kieselgel 60"--Trade Mark)
  3. washeluting with dichloromethane:methanol 19:1
  4. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-bb116577134747e896cc8f437c506c79
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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