Potassium Carbonate → HCID 57961759, compound

HRID 541926Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=1>CN(C)C=O.O>[N+:30]([C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][NH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1)([O-:32])=[O:31]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tert-butyl (3-aminophenyl)carbamate (0.51 g, 2.4 mmol) and potassium carbonate (0.61 g, 4.4 mmol) in N,N-dimethylformamide (7 mL) was treated with a solution of 1-(bromomethyl)-3-nitrobenzene (0.50 g, 2.3 mmol) in N,N-dimethylformamide (3 mL) and stirred at 25° C. for 16 h. The reaction mixture was diluted with water (80 mL) and extracted with ethyl acetate (3×75 mL). The combined organic layers were washed with water (3×50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude residue. This material was purified by flash column chromatography to give the desired product (0.78 g, 88% [90% pure]) as a solid. LCMS for C18H22N3O4 (M+H)+: m/z=344.2.

Workup

extractionextracted with ethyl acetate (3×75 mL)
washThe combined organic layers were washed with water (3×50 mL) and brine (50 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated
customto give a crude residue
customThis material was purified by flash column chromatography

Sources & evidence

ORD record: ord-210a6fa3a8be49cfa1890f0452d1c76d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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