Trimethylsilyldiazomethane → HCID 58659662, compound

HRID 1676989Notes

Reaction equation

HRID 1676989 reaction equation
[Br:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][OH:23])[S:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[NH:10][C:9]=1[C:18]([NH2:20])=[O:19])(=[O:7])=[O:6].[CH3:24][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[Br:1][CH2:2][CH2:3][N:4]([CH2:21][CH2:22][OH:23])[S:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:24])[CH:15]=2)[NH:10][C:9]=1[C:18]([NH2:20])=[O:19])(=[O:6])=[O:7]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 58659623HCID 58659623, compound

Product 1

HCID 58659662HCID 58659662, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 3-{[(2-bromoethyl)(2-hydroxyethyl)amino]sulfonyl}-5-hydroxy-1H-indole-2-carboxamide, described in Step B of Example 51, in 2:1 dichloromethane/MeOH was added excess trimethylsilyldiazomethane (solution in hexane). After stirring at room temperature for 16 hours, the mixture was concentrated in vacuo. Purification by preparative reversed phase HPLC afforded the titled product. HRMS (ES) exact mass calculated for C14H18BrN3O5S (M+H+): 420.0224. Found 420.0221.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customPurification by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-414ce782b906492eac7fdca977eeca20
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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