Water → 3-[1-(3-cyanopropyl)-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 1421189Notes

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)[NH:13][C:14](=[O:33])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH2:27]OS(C)(=O)=O)[CH:17]=2)=[CH:3]1.[C-:35]#[N:36].[Na+].[OH2:38]>CS(C)=O>[C:35]([CH2:27][CH2:26][CH2:25][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([C:15]2[C:14](=[O:33])[NH:13][C:12](=[O:38])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:17]1)#[N:36]

Participants

Conditions

Temperature: 50 °C

Procedure

450 mg of the product of Example 58 in 20 ml of DMSO were treated with 116 mg of sodium cyanide. The mixture was heated at 50° C. for 8 hours, then cooled and poured into water. The mixture was extracted with ethyl acetate and the extracts were dried. Concentration and chromatography on silica gel with toluene/ acetic acid (9:1) gave a solid which was triturated with diethyl ether, filtered off and dried. There were obtained 69 mg of 3-[1-(3-cyanopropyl)-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 245°-247° C.

Workup

temperaturecooled
extractionThe mixture was extracted with ethyl acetate
customthe extracts were dried
concentrationConcentration and chromatography on silica gel with toluene/ acetic acid (9:1)
customgave a solid which
customwas triturated with diethyl ether
filtrationfiltered off
customdried

Sources & evidence

ORD record: ord-06697c1a7b5d491c88f8c1e94ee1e5d4
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE036736

Reaction notes

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