Sodium hydride → HCID 10439304, compound

HRID 1735497Notes

Reaction equation

HRID 1735497 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[NH:15][C:16]3[C:28]4[NH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][C:25]=5[O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[C:20]=4[C:19]4[C:37](=[O:41])[NH:38][C:39](=[O:40])[C:18]=4[C:17]=3[C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:44]([O:51][CH2:52]Cl)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C.O>[CH2:44]([O:51][CH2:52][N:38]1[C:39](=[O:40])[C:18]2[C:17]3[C:13]4[C:14](=[C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:10]=[CH:11][CH:12]=4)[NH:15][C:16]=3[C:28]3[NH:27][C:26]4[C:25]([O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:24][CH:23]=[CH:22][C:21]=4[C:20]=3[C:19]=2[C:37]1=[O:41])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 10459854HCID 10459854, compound

Product 1

HCID 10439304HCID 10439304, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

143.8 mg of 1,11-dibenzyloxy-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione was dissolved in 50 ml of DMF, 128.8 mg of 60% oily sodium hydride (NaH) was added, 36.5 μl of benzyloxymethyl chloride was gradually added under ice cooling over a period of 10 minutes, and the mixture was subjected to reaction at 0° C. for further 1 hour. The reaction solution was diluted with water and extracted with ethyl acetate, the ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Kiezel gel 60; eluted with chloroform) to give the desired 6-benzyloxymethyl-1,11-dibenzyloxy-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (yield: 61.7%).

Workup

  1. customthe mixture was subjected to reaction at 0° C. for further 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialthe ethyl acetate layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Kiezel gel 60; eluted with chloroform)

Sources & evidence

ORD record
ord-0fbf9a6409d14abb92b60aa58612be0c
Source dataset
uspto-grants-1996_07
Patent number
US05536827

Reaction notes

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