N-(3-Aminophenyl)-1-phenylmethanesulfonamide → tert-butyl 2-(2-((3-(phenylmethylsulfonamido)phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate

HRID 537861Notes

Reaction equation

Cl[C:2]1[O:3][C:4]([C:7]2[N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:5][N:6]=1.[NH2:23][C:24]1[CH:25]=[C:26]([NH:30][S:31]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=1>CC(O)C>[C:35]1([CH2:34][S:31]([NH:30][C:26]2[CH:25]=[C:24]([NH:23][C:2]3[O:3][C:4]([C:7]4[N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]5[C:14]([CH:15]=4)=[CH:13][CH:12]=[CH:11][CH:10]=5)=[CH:5][N:6]=3)[CH:29]=[CH:28][CH:27]=2)(=[O:32])=[O:33])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl 2-(2-chlorooxazol-5-yl)-1H-indole-1-carboxylate 21 (0.31 g, 0.974 mmol) and N-(3-aminophenyl)-1-phenylmethanesulfonamide 26 (3.1 g, 1.948 mmol) in 2-propanol (20 mL) was heated to 80° C. for 14 h with stirring. Upon cooling, solvent was evaporated and silica column purified (Biotage) (Acetone/hexane as an eluent) to provide tert-butyl 2-(2-((3-(phenylmethylsulfonamido)phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 28 (0.24 g, 45% yield) as solid. MS (ES) m/z 545 (M+H+).

Workup

temperatureUpon cooling
customsolvent was evaporated
customsilica column purified (Biotage) (Acetone/hexane as an eluent)

Sources & evidence

ORD record: ord-eee78ee571e949d685d55ea3f90b5ca9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865709B2

Reaction notes

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