Sodium Carbonate → tert-Butyl 4-(4-fluoro-5-nitro-2-vinylbenzamido)piperidine-1-carboxylate

HRID 2093797

Reaction equation

Cl[C:2]1[CH:23]=[C:22]([F:24])[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:5].[CH2:28](OB(C=C)OCCCC)[CH2:29]CC.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:24][C:22]1[C:21]([N+:25]([O-:27])=[O:26])=[CH:20][C:3]([C:4]([NH:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[O:5])=[C:2]([CH:28]=[CH2:29])[CH:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Under nitrogen, the mixture of tert-butyl 4-(2-chloro-4-fluoro-5-nitrobenzamido)piperidine-1-carboxylate (Step 1, 1.52 g, 3.88 mmol), vinylboronic acid dibutyl ester (0.86 mL, 3.88 mmol), dichlorobis(triphenylphosphine)palladium (II) (136 mg, 0.2 mmol) and sodium carbonate (2.9 g, 27.2 mmol) in THF (40 mL) and water (10 mL) was heated at 90° C. overnight. The reaction mixture was cooled to room temperature, partitioned between EtOAc and brine. The organic extracts were dried (Na2SO4), concentrated, and purified by silica gel chromatography (EtOAc/Hexanes:1/4) to afford tert-Butyl 4-(4-fluoro-5-nitro-2-vinylbenzamido)piperidine-1-carboxylate; ESMS m/z 394.2 (M+H+).

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between EtOAc and brine
dry with materialThe organic extracts were dried (Na2SO4)
concentrationconcentrated
custompurified by silica gel chromatography (EtOAc/Hexanes:1/4)

Sources & evidence

ORD record: ord-0b1f7f5a13934239807174631747a0f5
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445505B2

Linked notes

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