Ammonia → HCID 43554923, compound

HRID 873045Notes

Reaction equation

HRID 873045 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][C:7]=1[F:14].[NH3:19].[BH4-].[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:19])=[CH:8][C:7]=1[F:14]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 43554841HCID 43554841, compound

Product 1

HCID 43554923HCID 43554923, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 4-(3,4-difluorophenoxy)-3-fluorobenzaldehyde (300 mg, 1.19 mmol) and 7 M NH3 in MeOH (10 mL) was added titanium isopropoxide (0.712 mL, 2.38 mmol). The reaction mixture was stirred overnight at rt. Then, NaBH4 (54.0 mg, 1.43 mmol) was added in portions. The mixture was stirred at rt for 4 h, and quenched with water and filtered. The organic part was extracted with ethyl acetate. Combined organic portions were dried over Na2SO4, filtered and concentrated. Purification via Biotage reverse phase chromatography (acetonitrile/water, 5%-95% with 0.25% TFA) afforded the title product (100 mg) as a white solid.

Workup

  1. stirringThe mixture was stirred at rt for 4 h
  2. customquenched with water
  3. filtrationfiltered
  4. extractionThe organic part was extracted with ethyl acetate
  5. dry with materialCombined organic portions were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via Biotage

Sources & evidence

ORD record
ord-c61ba789dfe54c20bc92264a59369810
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

Loading…