Trimethylsilyldiazomethane → HCID 13370529, compound

HRID 1508486Notes

Reaction equation

HRID 1508486 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[N:18]([CH3:24])[N:17]=2)=[CH:12][CH:11]=1>CCOCC.CO.C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:20]=[C:19]([C:21]([O:23][CH3:1])=[O:22])[N:18]([CH3:24])[N:17]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 812168HCID 812168, compound

Product 1

HCID 13370529HCID 13370529, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Trimethylsilyldiazomethane (1.75 mL of a 2 M soln in Et2O, 3.49 mmol) was added to a stirred solution of 3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carboxylic acid (0.507 g, 2.182 mmol) in dry MeOH (2.2 mL) and dry CH2Cl2 (19.6 mL) at 25° C. under N2. The reaction was stirred at 25° C. for 2 h. The reaction mixture was concentrated in vacuo to afford methyl 3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carboxylate, as a colorless solid. LCMS calc.=247.11. found=247.03 (M+H)+. 1H NMR (600 MHz, CDCl3): δ 7.71 (d, J=8.5 Hz, 2H); 7.04 (s, 1H); 6.93 (d, J=8.5 Hz, 2H); 4.21 (s, 3H); 3.90 (s, 3H); 3.83 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b694133bf0914fff9843cb1d899ea138
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

Loading…