Diazomethane → HCID 15659342, compound

HRID 2255167Notes

Reaction equation

HRID 2255167 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[C:10]([CH2:27][CH:28]([CH3:30])[CH3:29])=[N+:11]([O-:26])[C:12]([OH:25])=[C:13]([CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:33])=[N-].B(Br)(Br)Br>ClCCl.CO.C(OCC)C.C(Cl)Cl>[C:1]([O:5][C:6]([O:8][C:9]1[C:10]([CH2:27][CH:28]([CH3:30])[CH3:29])=[N+:11]([O-:26])[C:12]([O:25][CH3:33])=[C:13]([CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 9550DiazomethaneHCID 25134Boron tribromideHCID 178441378HCID 178441378, compound

Product 1

HCID 15659342HCID 15659342, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

In 0.5 ml of dichloromethane-methanol (3:1) was dissolved 10 mg of 3-tert-butoxycarbonyloxy-6-hydroxy-5-(indol-3-yl)methyl-2-isobutylpyrazine 1-oxide. Thereto were added, under ice cooling, a solution of diazomethane dissolved in diethyl ether and 4-5 drops of a solution of 0.1 M of boron tribromide dissolved in methylene chloride. The container was cook-stoppered and the contents were stirred for 12 hours at room temperature. The contents were then diluted with 5 ml of dichloromethane, and the mixture was washed with an aqueous sodium hydrogen carbonate solution and dried over sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by a silica gel thin layer chromatography (dichloromethane:methanol=40:1) to obtain 3.6 mg of the title compound as a pale brown solid substance.

Workup

  1. additionThereto were added, under ice cooling
  2. washthe mixture was washed with an aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customThe residue was purified by a silica gel thin layer chromatography (dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-a060c7b408d346f1b4fda7b5c966f581
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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