Phenyl isocyanate → N-phenyl-5-(4-pyridinyl)-1-indolinecarboxamide

HRID 1510254Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH2:11][CH2:10]3)=[CH:3][CH:2]=1.[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[C:16]1([NH:22][C:23]([N:12]2[C:13]3[C:9](=[CH:8][C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[CH:15][CH:14]=3)[CH2:10][CH2:11]2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-(4-pyridinyl)indoline (80 mg) in acetonitrile (10 mL) was added phenyl isocyanate (53 mg) and the mixture was stirred at 80° C. for 6 hours. The mixture was evaporated to dryness and the residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (10:1) to give N-phenyl-5-(4-pyridinyl)-1-indolinecarboxamide (60 mg) as a light-brown powder.

Workup

customThe mixture was evaporated to dryness
customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (10:1)

Sources & evidence

ORD record: ord-a83376d050724920903d4a2a803ac128
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211919B2

Reaction notes

Loading…