Potassium Carbonate → HCID 58887654, compound

HRID 1767213Notes

Reaction equation

HRID 1767213 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-hydroxyphenyl)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/isohexane (15/85) to give the title compound. (160 mg, 92%). LC/MS [MH+] 556 Rt=5.5 min.

Workup

  1. filtrationThe reaction mixture was then filtered through highflo
  2. customevaporated down to an oil
  3. customchromatographed on a Water'

Sources & evidence

ORD record
ord-cc72c26f34f84e55bec14ce2ad4cac5d
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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