Trimethylsilyldiazomethane → HCID 22054249, compound

HRID 1830430Notes

Reaction equation

HRID 1830430 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[C:14]([CH2:16][C:17]3[C:18](=[O:29])[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21](=[O:24])[C:22]=3[CH3:23])[CH:13]=[CH:12][C:11]=2[OH:30])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:32][Si](C=[N+]=[N-])(C)C>CO>[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[C:14]([CH2:16][C:17]3[C:18](=[O:29])[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[C:21](=[O:24])[C:22]=3[CH3:23])[CH:13]=[CH:12][C:11]=2[O:30][CH3:32])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 22054307HCID 22054307, compound

Product 1

HCID 22054249HCID 22054249, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(2-Chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide (0.050 g, 0.113 mmol) was dissolved in methanol (5 ml) and after adding thereto 10% trimethylsilyldiazomethane (hexane solution) (3.5 ml), the solution was stirred at room temperature for 2 hours. The reaction solution was concentrated and the obtained residue was recrystallized from a mixed solvent of ether and hexane (1:1) to obtain the titled compound (0.051 g, 0.112 mmol, 99%).

Workup

  1. additionafter adding
  2. concentrationThe reaction solution was concentrated
  3. customthe obtained residue was recrystallized from a mixed solvent of ether and hexane (1:1)

Sources & evidence

ORD record
ord-e1b8d0a1305d4be89e046236a7364961
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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