HCID 18794872, compound → HCID 9886464, compound

HRID 1004211Notes

Reaction equation

HRID 1004211 reaction equation
CC(C)(C)C([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[C:7]([C:17]2[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=2[C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)=[CH:6]1)=O.O(C)[Na]>CO>[CH3:31][N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:21]2[C:20](=[O:32])[NH:19][C:18](=[O:33])[C:17]=2[C:7]2[C:8]3[C:13](=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)[NH:5][CH:6]=2)=[CH:23]1

Participants

4

Reactant 2

HCID 18794872HCID 18794872, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 9886464HCID 9886464, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure of Example 1, Step F, the N-deprotection reaction of 1.3 g (2.76 mmol) of 3-[1-(2,2-dimethyl-propionyl)-6-nitro-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (20) from Step D above with 4.3 ml (6.88 mmol) of a 1.6 molar solution of NaOCH3 in 65 ml of methanol yielded 300.6 mg (28.1%) of 3-(1-methyl-1H-indol-3-yl)-4-(6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (III) as a red solid after crystallization from ethyl acetate and hexane. mp>260° C. MS: (M+), m/z 386.

Sources & evidence

ORD record
ord-d4d7e71c136a412a8420e97bd2646e4e
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

Loading…