Hydrochloric Acid → HCID 21904621, compound

HRID 1990761Notes

Reaction equation

HRID 1990761 reaction equation
[BH4-].[Na+].[N:3]([CH2:6][C:7]1[CH:14]=[C:13]([F:15])[C:10]([C:11]#[N:12])=[C:9]([F:16])[CH:8]=1)=[N+]=[N-].Cl>O.C1COCC1.[Pd]>[NH2:3][CH2:6][C:7]1[CH:8]=[C:9]([F:16])[C:10]([C:11]#[N:12])=[C:13]([F:15])[CH:14]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21904647HCID 21904647, compound

Product 1

HCID 21904621HCID 21904621, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

This reaction was carried out according to the procedure described in J. Chem. Res. (M) (1992) 3128. To a suspension of 520 mg of 10% Pd/C (50% moisture) in 20 mL of water was added a solution of sodium borohydride (0.834 g, 0.0221 mol) in 20 mL of water. Some gas evolution resulted. 4-Azidomethyl-2,6-difluorobenzonitrile (1.26 g, 6.49 mmol; see step (v) above) was dissolved in 50 mL of THF and added to the aqueous mixture on an ice bath over 15 min. The mixture was stirred for 4 h, whereafter 20 mL of 2M HCl was added and the mixture was filtered through Celite. The Celite was rinsed with more water and the combined aqueous phase was washed with EtOAc and subsequently made alkaline with 2M NaOH. Extraction three times with methylene chloride followed and the combined organic phase was washed with water, dried (Na2SO4) and evaporated. Yield: 0.87 g (80%).

Workup

  1. customSome gas evolution resulted
  2. additionadded to the aqueous mixture on an ice bath over 15 min
  3. additionwas added
  4. filtrationthe mixture was filtered through Celite
  5. washThe Celite was rinsed with more water
  6. washthe combined aqueous phase was washed with EtOAc and subsequently made alkaline with 2M NaOH
  7. extractionExtraction three times with methylene chloride
  8. washthe combined organic phase was washed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-6da93d78da1f48c0b31a41326443d2b3
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

Loading…