HCID 57722716, compound → 2-Pyridineethanamine, beta,beta-difluoro-6-methyl-

HRID 1987069Notes

Reaction equation

HRID 1987069 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=1)([F:7])[F:6])=[N+]=[N-]>CO.[Pd]>[F:7][C:5]([F:6])([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=1)[CH2:4][NH2:1]

Participants

4

Reactant 1

HCID 57722716HCID 57722716, compound

Product 1

HCID 577227042-Pyridineethanamine, beta,beta-difluoro-6-methyl-Yield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(2-Azido-1,1-difluoro-ethyl)-6-methyl-pyridine (700 mg, 3.54 mmol), as prepared in the preceding step, in MeOH (10 mL) was treated with 10% Pd/C (150 mg) under 39 Psi H2 atmosphere overnight. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated to afford the product as a brown oil (605 mg, 99%). 1H NMR (CDCl3) δ 7.69 (t, J=7.74 Hz, 1H), 7.46 (d, J=7.70 Hz, 1H), 7.22 (d, J=7.81 Hz, 1H), 3.42 (t, J=14.40 Hz, 2H), 2.58 (s, 3H); LC/MS (m/z) [M+1] 173.2 (calculated for C8H11F2N2, 173.1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-726c58f0c62441ccb6a3a61a12155f1e
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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