1-Bromo-2,6-difluorobenzene → HCID 86727489, compound

HRID 519110Notes

Reaction equation

HRID 519110 reaction equation
[Br:1][C:2]1[C:7](F)=[CH:6][CH:5]=[CH:4][C:3]=1[F:9].[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>CN(C)C1C=CN=CC=1>[C:19]([O:18][C:16]([N:10]1[CH2:15][CH2:14][N:13]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([F:9])[C:2]=2[Br:1])[CH2:12][CH2:11]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 1235571-Bromo-2,6-difluorobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 86727489HCID 86727489, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-1,3-difluorobenzene (0.2 g, 1.03 mmol) and tert-butyl piperazine-1-carboxylate (0.39 g, 2.07 mmol), and N,N-dimethylpyridin-4-amine (0.06 g, 0.52 mmol) was stirred at 120° C. overnight. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 5% EtOAc in petroleum ether) to give 4-(2-bromo-3-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.06 g, 16%). 1H NMR (CDCl3, 400 MHz): δ 7.25 (m, 1H), 6.87 (m, 1H), 6.81 (d, J=8.4 Hz, 1H), 3.63 (t, J=4.8 Hz, 4H), 3.01 (t, J=4.8 Hz, 4H), 1.5 (s, 9H). LC/MS (Table 1, Method 2) Rt=1.300 min; MS m/z: 303 [M+H−56]+ and 305 [M+H−56]+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-5800dc93f3344d2a8cb3aacada6056fa
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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