Cyclopropylamine → 3-(Cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile

HRID 2364526Notes

Reaction equation

HRID 2364526 reaction equation
F[C:2]1[C:3]([C:16]#[N:17])=[N:4][CH:5]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1.[CH:18]1([NH2:21])[CH2:20][CH2:19]1>>[CH:18]1([NH:21][C:2]2[C:3]([C:16]#[N:17])=[N:4][CH:5]=[C:6]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[CH:7]=2)[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 694815193-Fluoro-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile

Product 1

HCID 694821863-(Cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrileYield 66%

Conditions

Temperature
75 °C

Procedure

3-Fluoro-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile (546 mg, 2.4 mmol) was taken up in cyclopropylamine (8 mL) and heated at 75° C. in a microwave for 10 minutes and then again for 12 minutes. The mixture was concentrated in vacuo and the residue was purified by silica gel chromatography to give 3-(cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile (417 mg, 66%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.93 (d, J=1.9 Hz, 1 H), 7.19 (dd, J=8.2, 5.9 Hz, 2 H), 7.19 (d, J=2.4 Hz, 1 H), 7.06 (t, J=8.6 Hz, 2 H), 5.02 (s, 1 H), 4.00 (s, 2 H), 2.48 (m, 1 H), 0.86 (m, 2 H), 0.61 (m, 2 H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0361dd7985034e30823b43b730f9c10a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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