Sodium borohydride → HCID 58297378, compound

HRID 238411Notes

Reaction equation

HRID 238411 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58297374HCID 58297374, compound

Product 1

HCID 58297378HCID 58297378, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice cooled solution of (E)-ethyl 3-(1-(4-bromophenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)acrylate (400 mg, 0.88 mmol) in 95% ethanol (10 mL) were added BiCl3 (554 mg, 1.76 mmol) and portionwise NaBH4 (134 mg, 3.52 mmol), then the resultant mixture was stirred at room temperature for 12 h. The reaction mixture was filtered, and the filtrate was partitioned between water (50 mL) and ethyl acetate (30 mL), the aqueous layer was extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by preparative TLC (eluting with 50% ethyl acetate in petroleum ether for three times) to give ethyl 3-(1-(4-bromophenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoate (5-2) (100 mg, yield: 25%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was partitioned between water (50 mL) and ethyl acetate (30 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (30 mL×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by preparative TLC (eluting with 50% ethyl acetate in petroleum ether for three times)

Sources & evidence

ORD record
ord-5e7f3963bf7a4fb2ad5eb22c5d3b0280
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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