Sodium borohydride → 1-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanol

HRID 1192490Notes

Reaction equation

HRID 1192490 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([OH:14])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 672495351-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanone

Product 1

HCID 672484331-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-[5-chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanone (0.032 g, 0.11 mmol) in methanol (0.3 mL) was added sodium tetrahydroborate (0.0040 g, 0.11 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 (33 mg, 100%). LCMS calculated for C17H14ClFNO(M+H)+: m/z=302.1; found: 302.0.

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-c7520f0704c043368ae4b9e7e47c048e
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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