HCID 57722726, compound → 2,2-Difluoro-2-(quinolin-8-yl)ethan-1-amine

HRID 1987064Notes

Reaction equation

HRID 1987064 reaction equation
[N:1]([CH2:4][C:5]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)([F:7])[F:6])=[N+]=[N-]>CO.[Pd]>[F:7][C:5]([F:6])([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)[CH2:4][NH2:1]

Participants

4

Reactant 1

HCID 57722726HCID 57722726, compound

Product 1

HCID 534287772,2-Difluoro-2-(quinolin-8-yl)ethan-1-amineYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 8-(2-azido-1,1-difluoro-ethyl)-quinoline (3.8 g, 16.24 mmol) in MeOH (20 mL), as prepared in the last step, was treated with 10 wt. % Pd—C (754 mg) and NH4HCO2 (3 g). After 45 minutes the reaction was filtered through a pad of Celite and partitioned between EtOAc (100 mL) and NaHCO3 (satd) (100 mL). The organic phase was washed with brine (100 mL), dried over Na2SO4 and concentrated in vacuo to afford the product as a yellow viscous oil (2.7 g). 1H NMR (300 Hz, CDCl3) δ 9.0-8.98 (m, 1H), 8.22-8.19 (m, 1H), 8.05 (d, J=7.3 Hz, 1H), 7.93 (d, J=8.2 Hz, 1H), 7.60 (t, J=7.7 Hz, 1H), 7.49-7.45 (m, 1H), 3.82 (t, J=15.3 Hz, 2H); LC/MS (m/z) [M+1]+ 209.2 (calculated for C11H10F2N2, 208.21).

Workup

  1. filtrationAfter 45 minutes the reaction was filtered through a pad of Celite
  2. custompartitioned between EtOAc (100 mL) and NaHCO3 (satd) (100 mL)
  3. washThe organic phase was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-850b7b37109f48dcb3b2d7937d3648a0
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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