Water → HCID 18971767, compound

HRID 2395412Notes

Reaction equation

HRID 2395412 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-(3hydroxy-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°-88° 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-73a0b6d140534f76ba4aeff422f9fc12
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

Loading…