Hydrochloric Acid → HCID 87426614, compound

HRID 623496Notes

Reaction equation

HRID 623496 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C:13]([F:18])([F:17])[CH:14]([F:16])[F:15])=[N:9][CH:10]=1)=[N+]=[N-].[ClH:19]>CO.[Pd]>[ClH:19].[F:18][C:13]([F:17])([CH:14]([F:16])[F:15])[CH2:12][O:11][C:8]1[N:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131734089HCID 131734089, compound

Product 1

HCID 87426614HCID 87426614, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 5-(azidomethyl)-2-(2,2,3,3-tetrafluoropropoxy)pyridine (110 mg, 2.1 mmol, Step-2) in methanol (3.5 mL) and 2M hydrochloric acid (0.2 mL) is added palladium 10% on carbon (10 mg). The mixture is stirred at room temperature under hydrogen atmosphere (1 atm) for 4 hours. The mixture is filtered through a pad of celite and washed with methanol. The filtrate is concentrated in vacuo to give 110 mg (93% yield) of the title compound as a white solid.

Workup

  1. filtrationThe mixture is filtered through a pad of celite
  2. washwashed with methanol
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-3b6313a56bac43139b3a6cc0784eba20
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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