Sodium borohydride → HCID 71149361, compound

HRID 920894Notes

Reaction equation

HRID 920894 reaction equation
C([O:3][C:4](=O)[C:5]([F:17])([F:16])[C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)C.[BH4-].[Na+]>C(O)C>[F:17][C:5]([F:16])([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10514875Ethyl α,α-difluoro-2-quinolineacetate

Product 1

HCID 71149361HCID 71149361, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of difluoroquinolin-2-yl acetic acid ethyl ester (2 g, 7.9 mmol) in ethanol (20 mL) was added NaBH4 (317 mg, 1.0 mmol) at 0° C. under N2. The mixture was stirred for 1 hour and then at room temperature for 1.5 hours. The solution was quenched with dilute HCl (0.1 N, 20 mL). The mixture was neutralized with saturated NaHCO3 solution and extracted with EtOAc (3*100 mL). The combined organic layer was dried over sodium sulfate. The solvent was evaporated and the residue was purified by column chromatography on silica gel (PE:EA=10:1) to give the title compound as a yellow solid (0.7 g, 44%). LC-MS (ESI+): m/e 210 (M+H)+, Rt: 0.75 min.

Workup

  1. waitat room temperature for 1.5 hours
  2. customThe solution was quenched with dilute HCl (0.1 N, 20 mL)
  3. extractionextracted with EtOAc (3*100 mL)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography on silica gel (PE:EA=10:1)

Sources & evidence

ORD record
ord-93853eac71ba43fe9968910bda919404
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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