Methanol → HCID 117760047, compound

HRID 709831Notes

Reaction equation

HRID 709831 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[C:6]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10](OC)=[O:11])#[N:2].CO.[BH4-].[Na+].[Cl-].[NH4+]>C1COCC1>[F:23][C:16]1[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=1[C:6]1[C:5]([CH2:4][CH2:3][C:1]#[N:2])=[CH:14][C:9]([CH2:10][OH:11])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 117760071HCID 117760071, compound

Product 1

HCID 117760047HCID 117760047, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 5-(2-cyanoethyl)-6-(2-fluoro-5-methoxyphenyl)nicotinate (548 mg), methanol (2 mL) and THF (10 mL) was added sodium borohydride (208 mg), and the mixture was refluxed for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (425 mg) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-87a0a0e3bef44ddfbfe362e7e4d00e7d
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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