Methylamine → HCID 68157900, compound

HRID 243259Notes

Reaction equation

HRID 243259 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.CN.C[CH2:21][N:22](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]([CH2:21][NH2:22])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 144194332-(2,6-Difluoro-3-nitrophenyl)pyridine

Product 1

HCID 68157900HCID 68157900, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(2,6-difluoro-3-nitrophenyl)pyridine (1.0 g, 4.2 mmol), methylamine (2.24 mL, 4.24 mmol, 2M in THF) and DIPEA (0.75 mL, 4.2 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 0-40% EtOAc/cyclohexane) to afford the title compound as a yellow solid (0.89 g, 84%). 1H NMR (CDCl3, 400 MHz): δ 8.74 (1H, ddd, 5.0, 2.1, 1.0 Hz) 8.46 (1H, br s) 8.27 (1H, dd, 9.5, 6.2 Hz), 7.80 (1H, td, 7.8, 2.1 Hz), 7.47 (1H, dq, 4.0, 1.2 Hz), 7.34 (1H, dd, 9.5, 8.2 Hz), 2.36 (3H, d, 5.3 Hz)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting residue was purified by chromatography (Si—PPC, gradient 0-40% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-8d28c85278104a7985b94437fda3ef6d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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