Sodium borohydride → HCID 22915642, compound

HRID 2260555Notes

Reaction equation

HRID 2260555 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])[CH:18]=[CH:17]3)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>O1CCCC1.CO>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])[CH:18]=[CH:17]3)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 15816899HCID 15816899, compound

Product 1

HCID 22915642HCID 22915642, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

440 mg (0.953 mmol) of methyl 2-{6-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]quinolin-2-yl}benzoate obtained in Example 1 were dissolved in a mixed solvent of 10 ml of tetrahydrofuran and 10 ml of methanol and the mixture was stirred. 40 mg (1.0 mmol) of sodium borohydride were added thereto and allowed to react at room temperature for one hour. After the reaction mixture was concentrated under reduced pressure, dichloromethane was added to the residue and the mixture was washed with a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate followed by filtration. The filtrate was concentrated under reduced pressure to obtain 368 mg of methyl 2-{6-[(2-butyl-4-chloro-5-hydroxymethyl-1H-imidazol-1-yl)methyl]quinolin-2-yl}benzoate.

Workup

  1. customto react at room temperature for one hour
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, dichloromethane
  3. additionwas added to the residue
  4. washthe mixture was washed with a saturated sodium chloride solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfollowed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49aea88ac38c4bb1872488af2fc9e4f3
Source dataset
uspto-grants-1995_12
Patent number
US05478832

Reaction notes

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