Water → HCID 18971767, compound

HRID 864352Notes

Reaction equation

HRID 864352 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:12]=[CH:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:19]1(Br)[CH2:23][CH2:22][CH2:21][CH2:20]1.[H-].[Na+].O>CN(C=O)C>[CH:19]1([O:1][C:2]2[CH:3]=[C:4]([N:10]3[C:18]4[CH:17]=[CH:16][N:15]=[CH:14][C:13]=4[N:12]=[CH:11]3)[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 18971808HCID 18971808, compound

Product 1

HCID 18971767HCID 18971767, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.05 g of 1-(3-hydroxy-4-methoxyphenyl)-1H-imidazo[4,5-c]pyridine, 2.5 g of cyclopentylbromide and 665 mg of NaH in 20 ml of DMF was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate, dried to give 1.4 g of crude product. Recrystallization from CH2Cl2 gave 574 mg product. M.P.: 66°-68° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. customto give 1.4 g of crude product
  4. customRecrystallization from CH2Cl2

Sources & evidence

ORD record
ord-5e57e1d5416f43cc9dc15e178e493c7a
Source dataset
uspto-grants-1996_10
Patent number
US05563143

Reaction notes

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