Bromocyclopentane → HCID 178488974, compound

HRID 582142Notes

Reaction equation

HRID 582142 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:11][CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:18]1([O:1][C:2]2[CH:3]=[C:4]([C:10]3[NH:11][CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 8728Bromocyclopentane2×HCID 11430Potassium Carbonate2×HCID 178488973HCID 178488973, compound

Product 1

HCID 178488974HCID 178488974, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(3-hydroxy-4-methoxyphenyl)-imidazole-4-formamide (110 mg, 0.47 mmol), cyclopentyl bromide (60 μl, 0.56 mmol) and K2CO3 (162 mg, 1.2 mmol) in DMF (10 ml) were heated at 70° C. overnight. A further quantity of cyclopentyl bromide (60 μl, 0.56 mmol) and K2CO3 (162 mg, 1.2 mmol) were added and the reaction mixture was cooled to room temperature, diluted with water (50 ml), extracted with ethyl acetate (2×100 ml). The combined organics were washed with brine (30 ml) dried over Na2SO4 and the volatiles removed in vacuo. Flash chromatography (SiO2 ; CH2Cl2 :EtOH (9:1) (1% NH3)) afforded 2-(3-cyclopentyloxy-4-methoxyphenyl)-imidazole-4-formamide (43 mg,) as a white solid, mp d.>195° C.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined organics were washed with brine (30 ml)
  4. dry with materialdried over Na2SO4
  5. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-4125746db8464844a1aaf4f858840f2b
Source dataset
uspto-grants-1999_07
Patent number
US05922751

Reaction notes

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