Isopropylamine → HCID 68157042, compound

HRID 243256Notes

Reaction equation

HRID 243256 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[CH:18]([NH2:21])([CH3:20])[CH3:19].CCN(C(C)C)C(C)C>C(#N)C>[F:11][C:4]1[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[C:2]([NH:21][CH:18]([CH3:20])[CH3:19])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 144194332-(2,6-Difluoro-3-nitrophenyl)pyridine

Product 1

HCID 68157042HCID 68157042, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(2,6-difluoro-3-nitrophenyl)pyridine (0.85 g, 3.6 mmol), isopropylamine (0.31 mL, 3.6 mmol) and DIPEA (0.63 mL, 3.6 mmol) in acetonitrile (10 mL) was stirred overnight at RT. The mixture was concentrated in vacuo and the resulting residue was purified by chromatography (Si—PPC, gradient 0-50% EtOAc/cyclohexane) to afford the title compound as a yellow oil (0.49 g, 50%). 1H NMR (CDCl3, 400 MHz): δ 8.76 (1H, ddd, J=6.5, 3.7, 2.4 Hz), 8.26 (1H, dd, J=12.7, 8.1 Hz), 7.86 (1H, br s), 7.81 (1H, td, J=10.4, 2.5 Hz), 7.46 (1H, dq, J=10.5, 1.5 Hz), 7.34 (1H, ddd, J=10.2, 6.5, 1.6 Hz), 6.57 (1H, dd, J=12.7, 10.8 Hz), 2.70-2.54 (1H, m), 0.93 (6H, d, J=8.4 Hz)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting residue was purified by chromatography (Si—PPC, gradient 0-50% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-f5f10244d1cc47e0aa53aadf05d965a8
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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