Potassium Carbonate → 1,1-Dimethylethyl 7-[(2-fluoro-4-nitrophenyl)oxy]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 641563Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[C:12]([O:16][C:17]([N:19]1[CH2:25][CH2:24][C:23]2[CH:26]=[C:27]([OH:30])[CH:28]=[CH:29][C:22]=2[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:30][C:27]1[CH:28]=[CH:29][C:22]2[CH2:21][CH2:20][N:19]([C:17]([O:16][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:18])[CH2:25][CH2:24][C:23]=2[CH:26]=1

Participants

Conditions

Temperature: 130 °C

Procedure

3,4-difluoronitrobenzene (664 mg, 4.18 mmol) was added to a mixture of 7-hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester (WO 02/40471) (1 g, 3.8 mmol) and potassium carbonate (1.3 g, 9.49 mmol) in dimethylformamide (10 ml) and the reaction heated at 130° C. for 3 hours. The reaction was cooled, diluted with ethyl acetate, washed with water and then with a mixture of water:brine (1:1), dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ethyl acetate:pentane (1:10) to afford the title compound. MS (ES+) m/e 303 [M-COOtBu]+.

Workup

temperatureThe reaction was cooled
washwashed with water
additionwith a mixture of water:brine (1:1)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography
washeluting with a mixture of ethyl acetate:pentane (1:10)

Sources & evidence

ORD record: ord-1a9b81b0b2d846e29be03887c239cd45
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696193B2

Reaction notes

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