Ammonium Hydroxide → 3-(1-methylindol-3-yl)4-[3-(2-morpholin-4-ylethyloxy)phenyl]-1H-pyrrole-2,5-dione

HRID 1017564Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[O:13][C:14](=O)[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:17]=2)=[CH:3]1.[OH-].[NH4+:34]>CN(C=O)C.O.CO.C(Cl)Cl>[NH4+:2].[OH-:13].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[NH:34][C:14](=[O:13])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:17]=2)=[CH:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

3-(1-Methylindol-3-yl)-4-[3-(2-morpholin-4-ylethyloxy)phenyl]furan-2,5-dione was then dissolved in DMF (5 mL) and ammonium hydroxide (10 mL) was added. The resulting mixture was heated at 140° C. for 4 h, then cooled to room temperature, and diluted with water. The product was extracted into EtOAc. The EtOAc layer was washed with NaCl (sat.) and dried over sodium sulfate. Purificaiton on a silica gel column with 5% (10% NH4OH in MeOH) in CH2Cl2 gave 3-(1-methylindol-3-yl)4-[3-(2-morpholin-4-ylethyloxy)phenyl]-1H-pyrrole-2,5-dione (0.21 g, >99% yield).

Workup

temperaturecooled to room temperature
extractionThe product was extracted into EtOAc
washThe EtOAc layer was washed with NaCl (sat.)
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-dfe650e420f54202a398323a2b199f5d
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479490B2

Reaction notes

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