Sodium borohydride → HCID 58565346, compound

HRID 2175327Notes

Reaction equation

HRID 2175327 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17](=[O:19])[CH3:18])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH:17]([OH:19])[CH3:18])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58565344HCID 58565344, compound

Product 1

HCID 58565346HCID 58565346, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethanone (0.27 g, 1.1 mmol) in methanol (6 mL) was added sodium tetrahydroborate (41 mg, 1.1 mmol). The reaction was stirred at room temperature for 1 hour, quenched with water, and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give title compound (0.26 g). The crude product was used directly in the next step. LCMS calculated for C16H13FN(M-OH)+: m/z=238.1. Found: 238.1.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-60821f8ad1fa49eeaea5332fca0ac192
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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