Sodium borohydride → HCID 68488240, compound

HRID 1945288Notes

Reaction equation

HRID 1945288 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:30]([Cl:31])=[CH:29][C:13]3[NH:14][C:15]([O:17][C:18]4[CH:19]=[CH:20][C:21]([CH3:28])=[C:22]([CH:27]=4)[C:23]([O:25][CH3:26])=[O:24])=[N:16][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.O>[Cl:31][C:30]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][CH:8]=2)=[CH:11][C:12]2[N:16]=[C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([CH3:28])=[C:22]([CH:27]=3)[C:23]([O:25][CH3:26])=[O:24])[NH:14][C:13]=2[CH:29]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68490381HCID 68490381, compound

Product 1

HCID 68488240HCID 68488240, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a 0° C. solution of methyl 5-{[5-(4-acetylphenyl)-6-chloro-1H-benzimidazol-2-yl]oxy}-2-methylbenzoate (50 mg, 0.115 mmol) in MeOH (2 mL) was added NaBH4 (6.5 mg, 0.172 mmol). The mixture was warmed to rt and stirred for 15 min. Water (5-6 drops) was added and the mixture was concentrated. The residue was partitioned between Et2O and water. The aqueous phase was extracted with Et2O. The combined ethereal extracts were washed with brine, dried (MgSO4), filtered, and concentrated to afford the desired product, which was used in the next step without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between Et2O and water
  3. extractionThe aqueous phase was extracted with Et2O
  4. washThe combined ethereal extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06017660a62c4dabb6db8de89ffdd197
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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