2,4-Difluoronitrobenzene → HCID 62416746, compound

HRID 242947Notes

Reaction equation

HRID 242947 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([NH2:16])[CH2:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>CC#N>[CH:12]1([NH:16][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 75645CyclobutylamineHCID 81531Diisopropylethylamine

Product 1

HCID 62416746HCID 62416746, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,4-difluoro-1-nitrobenzene (0.7 mL, 6.3 mmol) in CH3CN (10 mL) were added cyclobutylamine (0.54 mL, 6.3 mmol) and DIPEA (1.1 mL, 6.3 mmol). The reaction mixture was stirred at RT for 18 h then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% EtOAc in cyclohexane) to afford cyclobutyl-(5-fluoro-2-nitrophenyl)amine as a yellow oil (1.38 g, quantitative). To a solution of the product thus obtained (6.3 mmol) in EtOAc (60 mL) was added 10% Pd/C (150 mg) and the reaction mixture stirred at RT for 18 h under a hydrogen atmosphere. The suspension was filtered through a pad of Celite® and the filtrate concentrated in vacuo to afford the title compound as an orange oil (1.1 g, quantitative). 1H NMR (CDCl3, 300 MHz): δ 6.63-6.56 (1H, m), 6.35-6.19 (2H, m), 3.92-3.78 (1H, m), 3.66-2.91 (2H, m), 2.53-2.36 (2H, m), 1.94-1.73 (4H, m).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-3d186477106a40b68a64235316c0803a
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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