Water → HCID 69365961, compound

HRID 2284676Notes

Reaction equation

[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:16]1[CH:17]=[C:18]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C(OCC)(=O)C>[N+:22]([C:18]1[CH:17]=[C:16]([N:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)[CH:21]=[CH:20][CH:19]=1)([O-:24])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-Boc-hexahydro-1,4-diazepine (150 mg), 3-bromonitrobenzene (125 mg) and cesium carbonate (507 mg) in 1,4-dioxane (3 mL), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (26 mg) was added at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added to the mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 70% hexane in ethyl acetate) to obtain tert-butyl 4-(3-nitrophenyl)-1,4-diazepane-1-carboxylate (C27, 15 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed with saturated aqueous sodium chloride
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 70% hexane in ethyl acetate)

Sources & evidence

ORD record: ord-62b5abf5f20349e2a36f0d9ce3320172
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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