Potassium Carbonate → HCID 58887674, compound

HRID 1767216Notes

Reaction equation

HRID 1767216 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH2:16][CH2:15][CH2:14][C:13]=2[C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=2[OH:24])[N:7]=1)=[O:5])[CH3:2].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O.C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH2:16][CH2:15][CH2:14][C:13]=2[C:17]2[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 135971683HCID 135971683, compound

Product 1

HCID 58887674HCID 58887674, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21584184Diethylether waterSolvent

Procedure

A mixture of 6-[2-(5-methyl-2-hydroxyphenyl)cyclopent-1-enyl]pyridine-2-carboxylic acid ethyl ester (129 mg, 0.4 mmol), 4-fluorobenzyl bromide (83 mg, 0.44 mmol) and potassium carbonate (138 mg, 1 mmol) in acetone (4 ml) was stirred and refluxed for 20 hours. After cooling the mixture was diluted with water/diethyl ether and the organic phase dried (magnesium sulphate) evaporated and purified by chromatography on silica (8% ethyl acetate in iso-hexane) to give the title compound as a colourless gum (148 mg, 86%). 1H NMR (CDCl3)δ:1.41 (3H, t, J=7 Hz), 2.04–2.09 (2H, m), 2.18 (3H, s), 2.88–2.91 (2H, m), 3.11–3.15 (2H,m), 4.41 (2H, q, J=7 Hz), 4.91 (2H, s), 6.80 (1H, d, J=8 Hz), 6.87 (1H, d, J=2 Hz), 6.95–7.04 (4H, m), 7.17–7.21 (2H, m), 7.40 (1H, t, J=8 Hz), 7.79 (1H, d, J=8 Hz).

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureAfter cooling the mixture
  3. dry with materialthe organic phase dried (magnesium sulphate)
  4. customevaporated
  5. custompurified by chromatography on silica (8% ethyl acetate in iso-hexane)

Sources & evidence

ORD record
ord-2672dd34e23142389e4371c8f0218b67
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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