Potassium Carbonate → HCID 58887654, compound

HRID 1767193Notes

Reaction equation

HRID 1767193 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:22])=[C:6]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:13]2[N:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[CH:15][CH:14]=2)[CH:7]=1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][O:20][C:19]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:9]3[CH2:10][CH2:11][CH2:12][C:8]=3[C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:22][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([Cl:23])=[CH:25][CH:26]=3)[N:18]=2)=[O:21])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 135971684HCID 135971684, compound

Product 1

HCID 58887654HCID 58887654, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

6-{2-[5-Chloro-2-(hydroxy)-phenyl]-cyclopent-1-enyl}-pyridine-2-carboxylic acid (97 mg, 0.30 mmol) was refluxed in 2-butanone (4 mL) with 4-chlorobenzyl bromide (140 mg, 0.70 mmol) and potassium carbonate (1.0 g) under nitrogen for five hours. The reaction mixture was then filtered through highflo, evaporated down to an oil and chromatographed on a Water's sep-pak (10 g) with ether/iso-hexane (15/85) to give (160 mg, 92%).

Workup

  1. filtrationThe reaction mixture was then filtered through highflo
  2. customevaporated down to an oil
  3. customchromatographed on a Water'
  4. customto give (160 mg, 92%)

Sources & evidence

ORD record
ord-9def62a89bd64a4b83c8b6dd4d66c204
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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