Pyrazole → HCID 86702093, compound

HRID 715835Notes

Reaction equation

HRID 715835 reaction equation
[Br:1][C:2]12[CH2:12][C:6]3(CO)[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([CH3:15])([CH2:5]3)[CH2:3]1)[CH2:9]2.[NH:16]1[CH:20]=[CH:19][CH:18]=[N:17]1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Br:1][C:2]12[CH2:12][C:6]3([N:16]4[CH:20]=[CH:19][CH:18]=[N:17]4)[CH2:5][C:4]([CH3:15])([CH2:10][C:8]([CH3:11])([CH2:7]3)[CH2:9]1)[CH2:3]2

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 4622928CyanomethylenetributylphosphoraneHCID 86702092HCID 86702092, compound

Product 1

HCID 86702093HCID 86702093, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the 5-bromo-3,7-dimethyltricyclo[3.3.1.13,7]dec-1-ylmethanol (8.0 g, 29.3 mmol) in toluene (60 mL) was added 1H-pyrazole (1.55 g, 22.7 mmol) and cyanomethylenetributylphosphorane (2.0 g, 29.3 mmol) under nitrogen. After the addition, the mixture was stirred at 90° C. overnight. The reaction mixture was then concentrated, and the residue was purified by normal phase chromatography to give the title compound.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue was purified by normal phase chromatography

Sources & evidence

ORD record
ord-35dced0aa75d46198b101b7f8e774b1a
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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