Bromocyclopentane → HCID 59187449, compound

HRID 1944506Notes

Reaction equation

HRID 1944506 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:13][O:14][C:15]3[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[C:17]([CH3:26])[CH:16]=3)[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:27]([O-])([O-])=O.[K+].[K+].[CH:33]1(Br)[CH2:37][CH2:36][CH2:35][CH2:34]1>CC(C)=O>[CH:33]1([O:1][C:2]2[CH:3]=[C:4]([C:8]3[N:9]=[C:10]([CH2:13][O:14][C:15]4[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21]([O:23][CH3:27])=[O:22])=[C:17]([CH3:26])[CH:16]=4)[S:11][CH:12]=3)[CH:5]=[CH:6][CH:7]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 68544989HCID 68544989, compound

Product 1

HCID 59187449HCID 59187449, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(4-((4-(3-hydroxyphenyl)thiazol-2-yl)methoxy)-2-methylphenoxy)acetic acid (20 mol, 0.052 mmol) is dissolved in acetone (4 mL). K2CO3 (21 mg, 0.156 mmol) is added, followed by cyclopentyl bromide (38 μL, 0.259 mmol) and the resulting mixture is heated to reflux for 18 h. The solvent is evaporated in vacuo to give crude methyl 2-(4-((4-(3-(cyclopentyloxy)phenyl)thiazol-2-yl)methoxy)-2-methylphenoxy)acetate, which is used in Step B without further purification.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 18 h
  3. customThe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-cb4d9648f5bf4864b34ceb41819ca2f2
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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