Trimethylsilyldiazomethane → HCID 21252858, compound

HRID 1531006Notes

Reaction equation

HRID 1531006 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:14]3=[C:15]([C:17](=[O:20])[CH:18]=[CH:19][N:13]3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)[CH:16]=1)([OH:3])=[O:2].[CH3:21][Si](C=[N+]=[N-])(C)C>O1CCCC1.CO>[CH3:21][O:2][C:1]([C:4]1[CH:5]=[C:6]2[C:14]3=[C:15]([C:17](=[O:20])[CH:18]=[CH:19][N:13]3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)[CH:16]=1)=[O:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 21252828HCID 21252828, compound

Product 1

HCID 21252858HCID 21252858, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-carboxy-4H-pyrido[3,2,1-jk]carbazole-4-one (500 mg) produced in Example 175 was suspended in tetrahydrofuran (100 ml), and methanol (several drops) was added to the suspension. Trimethylsilyldiazomethane (2M hexane solution, 1 ml) was added dropwise at room temperature, and the mixture was stirred for 90 minutes. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel flash column chromatography (eluent: ethyl acetate) to obtain the title compound (250 mg, 48%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-88aef480d28a4c01b25fc40d70938e80
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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