Water → [2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid tert-butyl ester

HRID 1051227Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]2[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:24])=[C:10]([N+:25]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O>P(OCC)(OCC)OCC>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:9]=[C:10]2[C:11]([CH:14]=[C:15]([C:16]3[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:24])[NH:25]2)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of {4-[(E)-2-(2-chloro-6-methoxy-phenyl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (240 mg, 0.59 mmol) in triethyl phosphite (5.0 ml) was refluxed for 3 h. The reaction mixture was cooled to 25° C., and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded [2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid tert-butyl ester (140 mg, 63%) as a white solid. MH+ 373.0.

Workup

extractionThe aqueous phase was extracted three times with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over magnesium sulfate
filtrationFiltration
concentrationfollowed by concentration in vacuo
customgave a brown solid

Sources & evidence

ORD record: ord-c1501465f2d5413097d9a71e412e122d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388166B2

Reaction notes

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