2,4-Difluoronitrobenzene → HCID 68157024, compound

HRID 242998Notes

Reaction equation

HRID 242998 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].[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH2:23])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>CC#N>[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH:23][C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Product 1

HCID 68157024HCID 68157024, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-difluoro-1-nitrobenzene (3.69 g, 23.2 mmol), 3-aminoazetidine-1-carboxylic acid tert-butyl ester (4.0 g, 23.2 mmol) and DIPEA (3.97 mL, 23.2 mmol) in CH3CN (37 mL) was stirred at RT for 18 h under an argon atmosphere. The volatiles were removed in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane) to afford the title compound as a yellow solid (4.84 g, 67%). LCMS (Method B): RT 3.80 min [M+H]+ 312.1.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-1f2067c447a24d8da21fcbdbb4f7288f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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