Benzyl chloroformate → 4-(5-Bromo-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid benzyl ester

HRID 912896Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Br:12][C:13]1[CH:14]=[C:15]([C:25]([F:28])([F:27])[F:26])[C:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:17][CH:18]=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH2:5]([O:4][C:2]([N:22]1[CH2:23][CH2:24][N:19]([C:16]2[C:15]([C:25]([F:28])([F:26])[F:27])=[CH:14][C:13]([Br:12])=[CH:18][N:17]=2)[CH2:20][CH2:21]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyl chloroformate (806 μL, 5.7 mmol, Aldrich) was added dropwise to a mixture of 1-(5-bromo-3-trifluoromethyl-pyridin-2-yl)-piperazine (1.6 g, 5.2 mmol, Example 112a) and diisopropylethylamine (1.1 mL, 6.24 mmol, Aldrich) in dichloromethane (35 mL) with stirring at 0° C. The mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography (2%-100% EtOAc/hexane) to give the title compound as an orange oil. MS (ESI, positive ion) m/z: 444 (M+1).

Workup

stirringThe mixture was stirred at room temperature for 16 h
customThe solvent was removed in vacuo
customthe residue was purified by silica gel column chromatography (2%-100% EtOAc/hexane)

Sources & evidence

ORD record: ord-37a59bb54d1c4fb192d5df92c3bd6218
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026241B2

Reaction notes

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