Sodium borohydride → HCID 67246913, compound

HRID 1192475Notes

Reaction equation

HRID 1192475 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:19](=[O:21])[CH3:20])=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:5]=[C:6]([F:8])[CH:7]=1.[BH4-].[Na+]>CO>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:10]([CH:19]([OH:21])[CH3:20])=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67248764HCID 67248764, compound

Product 1

HCID 67246913HCID 67246913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-[8-(3,5-difluorophenyl)quinolin-7-yl]ethanone (0.057 g, 0.20 mmol) in methanol (0.5 mL) was added sodium tetrahydroborate (0.0076 g, 0.20 mmol). The reaction was stirred at room temperature for 1 hour, quenched with saturated sodium bicarbonate, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resulting residue was used in next step (48 mg, 84.1%). LCMS calculated for C17H14F2NO(M+H)+: m/z=286.1; found: 286.0.

Workup

  1. customquenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-67ca755629b0456a951d3eee7f243416
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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