Dimethylformamide → t-Butyl 2-(4-amino-2-((2'-fluorobiphenyl-4-yl)oxy)-5-nitrophenyl)pyrrolidine-1-carboxylate

HRID 13400Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[NH2:26][C:27]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][C:30]([CH:36]2[CH2:40][CH2:39][CH2:38][N:37]2[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[C:29](F)[CH:28]=1>C(OCC)(=O)C>[NH2:26][C:27]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][C:30]([CH:36]2[CH2:40][CH2:39][CH2:38][N:37]2[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[C:29]([O:14][C:11]2[CH:10]=[CH:9][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[CH:13][CH:12]=2)[CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

200 mg of 2′-fluorobiphenyl-4-ol and 184 mg of potassium carbonate were added to an N,N-dimethylformamide (3 ml) solution of 288 mg of t-butyl 2-(4-amino-2-fluoro-5-nitrophenyl)pyrrolidine-1-carboxylate, and the reaction liquid was stirred overnight at 80° C. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1) to obtain the entitled compound as a yellow solid.

Workup

customthe reaction liquid
customThe reaction liquid
washwashed with water and saturated saline in order
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated away
customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record: ord-88334f19c84844df8c80809518875144
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Reaction notes

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