Potassium Carbonate → {4-[4-(5-Chloro-pyridin-2-ylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid tert-butyl ester

HRID 605213

Reaction equation

Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=2)=[O:7])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[C:21]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:24]([O:23][C:21](=[O:22])[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:2]2[CH:17]=[CH:16][C:5]([C:6](=[O:7])[NH:8][C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][N:10]=3)=[CH:4][C:3]=2[N+:18]([O-:20])=[O:19])=[CH:33][CH:34]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of the product of Example 199A (300 mg, 0.9612 mmol) in anhydrous N,N-dimethylformamide (5 mL) was treated with N-Boc-4-hydroxyaniline (201 mg, 0.9612 mmol) and potassium carbonate (266 mg, 1.922 mmol) at room temperature, then heated at 80° C. under a nitrogen atmosphere for 5 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. The residue was taken up in ethyl acetate (100 mL) and washed with water (4×50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo. Trituration with 5% ethyl acetate gave the title compound (284 mg, 61%).

Workup

temperatureThe reaction was cooled to room temperature
customthe solvent removed by rotary evaporation in vacuo
washwashed with water (4×50 mL) and brine (50 mL)
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated by rotary evaporation in vacuo

Sources & evidence

ORD record: ord-c8749a8574984cab809137d791ee5269
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Linked notes

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