Diethyl Ether → HCID 68824608, compound

HRID 655834Notes

Reaction equation

HRID 655834 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=[O:11])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][Si](C=[N+]=[N-])(C)C.C(OCC)C>C1(C)C=CC=CC=1.CO>[CH3:18][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([N:6]2[C:2]([NH2:1])=[C:3]([C:16]#[N:17])[CH:4]=[N:5]2)[CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 167693Trimethylsilyldiazomethane2×HCID 16772929HCID 16772929, compound

Product 1

HCID 68824608HCID 68824608, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Conditions

Temperature
0 °C

Procedure

Title compound 8A, 3-(5-amino-4-cyanopyrazol-1-yl)benzoic acid (3.2 g, 1.0 eq, 14.04 mmol) was suspended in a toluene/methanol [3:1] solution (70 ml). This was then cooled to 0° C. and trimethylsilyldiazomethane was added drop wise as a 2M solution in diethyl ether (7.7 ml, 1.1 eq, 15.44 mmol). The reaction was allowed to warm to room temperature over 2 hours. A further portion of trimethylsilyidiazomethane (1.54 ml, 0.2 eq, 2.8 mmol) was added. The reaction was stirred at room temperature for a further 45 minutes and solvent was then removed in vacuo to give the title compound as an orange solid (3.4 g, 14.04 mmol, 100%). LCMS: [M+H]+=243, Rt=1.05 min, 100% purity.

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. customsolvent was then removed in vacuo

Sources & evidence

ORD record
ord-53a3aa9e4544447ba6ebac9f36e7c4df
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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