Trimethylsilyldiazomethane → HCID 86715753, compound

HRID 627625Notes

Reaction equation

HRID 627625 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][C:6](=[O:12])[NH:7]2.[CH3:13][Si](C=[N+]=[N-])(C)C>CO.C(Cl)Cl.C(#N)C>[CH3:13][O:12][C:6]1[CH:5]=[N:4][C:3]2[C:2]([NH2:1])=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 451217185-Aminoquinoxalin-2(1H)-one

Product 1

HCID 86715753HCID 86715753, compoundYield 34.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-aminoquinoxalin-2(1H)-one (440 mg, 2.73 mmol) in methanol (1 mL), DCM (8 mL) and acetonitrile (8 mL), at 0° C., was added TEA (1.14 mL, 8.19 mmol), followed by (trimethylsilyl)diazomethane (2 mL, 4.10 mmol; 2.0M in hexanes). The reaction mixture was allowed to warm to RT and stirred for additional 3 hours. The suspension was filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with 10%-50% ethyl acetate in hexane, to provide the title compound (167 mg, 0.953 mmol) as a light-yellow powder. LC/MS (ESI+) m/z=176 (M+H).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with 10%-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e1e88fa240024eba86c04129a77dcb3d
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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