Trimethylsilyldiazomethane → HCID 66934710, compound

HRID 2373355Notes

Reaction equation

HRID 2373355 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][C:6]([NH:8][C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=[O:7].[Si](C=[N+]=[N-])(C)(C)[CH3:20]>C(Cl)Cl.CO>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][C:6]([NH:8][C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([O:13][CH3:20])=[O:12])=[O:7]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 66934757HCID 66934757, compound

Product 1

HCID 66934710HCID 66934710, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Methoxy-4-oxobutanamido)nicotinic acid (ii-h-1) (1.28 g, 4.8 mmol) was dissolved in an equimolar mixture of CH2Cl2 and methanol (20 mL) and cooled to 0° C. TMS diazomethane (2M solution in diethyl ether; 5.2 mL, 10.6 mmol) was added dropwise. The mixture was stirred for 1 h and warmed to 23° C. Volatiles were removed under reduced pressure to provide ii-h as a pale yellow solid (1.37 g, 100%) MS m/z═267 (M+1).

Workup

  1. temperaturewarmed to 23° C
  2. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-46a81d2a25484874b19a1a5538c67028
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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