Sodium borohydride → HCID 89443811, compound

HRID 1771807Notes

Reaction equation

HRID 1771807 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:6][C:3]=1[CH:4]=O.[NH2:17][C:18]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([O:27][CH3:28])[C:19]=1[C:20]#[N:21].[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[F:26][C:25]1[C:18]([NH:17][CH2:4][C:3]2[CH:6]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)[CH:8]=[CH:9][C:2]=2[F:1])=[C:19]([C:22]([O:27][CH3:28])=[CH:23][CH:24]=1)[C:20]#[N:21]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 463122473′,4-Difluoro[1,1′-biphenyl]-3-carboxaldehydeHCID 82012920HCID 82012920, compound

Product 1

HCID 89443811HCID 89443811, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-fluoro-5-(3-fluorophenyl)benzaldehyde (505 mg, 2.32 mmol, 1.2 eq) and 2-amino-3-fluoro-6-methoxy-benzonitrile (320 mg, 1.93 mmol, 1 eq) in toluene (30 mL) was added 4 Å molecular sieves (10 g). The mixture was heated at reflux for 4 h, then filtered to remove the molecular sieves. The filtrate was concentrated and the residue obtained was dissolved in methanol (30 mL). NaBH4 (109.6 mg, 2.9 mmol, 1.5 eq) was added and the reaction stirred for 2 h at room temperature. The reaction was quenched by addition of water, and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 50:1) to give the title compound as an off-white solid (610 mg, 72%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. filtrationfiltered
  4. customto remove the molecular sieves
  5. concentrationThe filtrate was concentrated
  6. customthe residue obtained
  7. customThe reaction was quenched by addition of water
  8. extractionthe aqueous layer was extracted with EtOAc
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated in vacuo
  13. customThe residue obtained
  14. customwas purified by column chromatography (petroleum ether:EtOAc, 50:1)

Sources & evidence

ORD record
ord-88c98a9a917f43eaab3eeb1598336bd9
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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