Water → 1-ethyl-6-isopropoxy-2-[4-(2-oxo-oxazolidin-3-yl)-phenyl]-1H-indole-3-carbonitrile

HRID 907190Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5](=[O:30])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH2:28][CH3:29])[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=3)=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:28]([N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=2)[C:21]([C:22]#[N:23])=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([N:6]2[CH2:2][CH2:3][O:4][C:5]2=[O:30])=[CH:8][CH:9]=1)[CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of [4-(3-cyano-1-ethyl-6-isopropoxy-1H-indol-2-yl)-phenyl]-carbamic acid 2-chloro-ethyl ester (30 mg, 0.07 mmol) in DMF (1 mL) was added aqueous K2CO3 (10 mg) and then stirred at 50° C. for 18 h. The reaction mixture was poured into cold water and the precipitate collected by filtration and washed with hexane and dried in vacuo to afford the title compound (21 mg, 81%).

Workup

filtrationthe precipitate collected by filtration
washwashed with hexane
customdried in vacuo

Sources & evidence

ORD record: ord-a531488863b84b26a9257370c1a5af18
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013006B2

Reaction notes

Loading…