4-Bromoaniline → 1-(4-Bromophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

HRID 1470972Notes

Reaction equation

CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[Br:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1>CN(C=O)C>[Br:33][C:34]1[CH:40]=[CH:39][C:37]([N:38]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH:6]2[C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The product from Example 1C (0.7 g, 1.433 mmol) and 4-bromoaniline (2.54 g, 14.33 mmol) were suspended in DMF (6 mL) and stirred at 50° C. overnight. The resulting mixture was partitioned between ethyl acetate (100 mL) and water (50 mL). The organic phase was washed with 1N HCl (2×50 mL) followed by a brine wash then dried over MgSO4 filtered and concentrated. The crude product was purified by chromatography on silica gel using a solvent gradient of 2-50% ethyl acetate in hexane to give the title compound as a mixture of stereoisomers (74.4 mg, 11% yield).

Workup

customThe resulting mixture was partitioned between ethyl acetate (100 mL) and water (50 mL)
washThe organic phase was washed with 1N HCl (2×50 mL)
washwash
dry with materialthen dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by chromatography on silica gel using a solvent gradient of 2-50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-d687a17fb7b74381b290f1543697476c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006387B2

Reaction notes

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