Water → HCID 10459854, compound

HRID 1735496Notes

Reaction equation

HRID 1735496 reaction equation
[CH:1]1[CH:6]=[C:5]([OH:7])[C:4]2[NH:8][C:9]3[C:14]([C:3]=2[CH:2]=1)=[C:13]1[C:15]([NH:17][C:18](=[O:19])[C:12]1=[C:11]1[C:20]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[C:21]=2[NH:22][C:10]=31)=[O:16].C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>CN(C)C=O>[CH2:34]([O:27][C:23]1[C:21]2[NH:22][C:10]3[C:9]4[NH:8][C:4]5[C:3](=[CH:2][CH:1]=[CH:6][C:5]=5[O:7][CH2:14][C:3]5[CH:4]=[CH:5][CH:6]=[CH:1][CH:2]=5)[C:14]=4[C:13]4[C:15](=[O:16])[NH:17][C:18](=[O:19])[C:12]=4[C:11]=3[C:20]=2[CH:26]=[CH:25][CH:24]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 9928668133805-03-5

Product 1

HCID 10459854HCID 10459854, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

180.5 mg of BE-13793C (12,13-dihydro-1,11-dihydroxy-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)-dione) was dissolved in 137 ml of N,N-dimethylformamide (DMF), 510 mg of potassium carbonate was added, and 170 μl of benzyl bromide was added under ice cooling. The reaction solution was stirred at room temperature for 2 hours and, after addition of 200 ml of water, extracted with 200 ml of ethyl acetate, and the extract was dried over sodium sulfate and concentrated under reduced pressure to give 1,11-dibenzyloxy-12,13-dihydro-5H-indolo[ 2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (yield: 93.7%).

Workup

  1. extractionextracted with 200 ml of ethyl acetate
  2. dry with materialthe extract was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de5740a93a9548fc8647806fd5ab127e
Source dataset
uspto-grants-1996_07
Patent number
US05536827

Reaction notes

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