Indole → HCID 15065179, compound

HRID 2255166Notes

Reaction equation

HRID 2255166 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[C:12]([CH2:26][CH:27]([CH3:29])[CH3:28])=[N+:13]([O-:25])[C:14]([O:23][CH3:24])=[C:15]([CH2:17]OS(C)(=O)=O)[N:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1>C1(C)C=CC=CC=1>[CH2:3]([O:10][C:11]1[C:12]([CH2:26][CH:27]([CH3:29])[CH3:28])=[N+:13]([O-:25])[C:14]([O:23][CH3:24])=[C:15]([CH2:17][C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[NH:30][CH:31]=2)[N:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 15065178HCID 15065178, compound

Product 1

HCID 15065179HCID 15065179, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

300 Microliters of toluene and 3.7 mg of 60% sodium hydride were added to a mixture of 8.8 mg of 3-benzyloxy-5-mesyloxymethyl-2-isobutyl-6-methoxypyrazine 1-oxide and 8.2 mg of indole. The mixture was stirred for 16 hours at room temperature, and the reaction mixture was subjected to the same post-treatment as in Example B-1 to obtain 5.8 mg of 3-benzyloxy-5-(indol-3-yl)methyl-2-isobutyl-6-methoxypyrazine 1-oxide (Compound B-41) as colorless prismatic crystals having a melting point of 139.6°-141.9° C.

Sources & evidence

ORD record
ord-fed666b3032d4cfcbd1d91c0b3bf2c68
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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