Acetonitrile → HCID 68753409, compound

HRID 1876867Notes

Reaction equation

HRID 1876867 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.C(#N)C.[CH:18]1(/[CH:22]=[CH:23]/[C:24]#[N:25])[CH2:21][CH2:20][CH2:19]1.N12CCCN=C1CCCCC2>>[CH:18]1([CH:22]([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:23][C:24]#[N:25])[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67335599HCID 67335599, compound

Product 1

HCID 68753409HCID 68753409, compound

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (9.63 g, 0.0496 mol) in acetonitrile (124 mL, 2.37 mol) was added (E)-3-cyclobutylacrylonitrile (5.30 g, 0.0495 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (3.70 mL, 0.0248 mol). The resulting mixture was stirred at room temperature overnight, then evaporated to dryness. The mixture was purified on silica gel, eluting with 0 to 80% EtOAc in hexanes, to give the desired product as a racemic mixture (11.2 g, 75.2%). LCMS (M+H) 302.4.

Workup

  1. customevaporated to dryness
  2. customThe mixture was purified on silica gel
  3. washeluting with 0 to 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-3b0dca6f780e43e5b0f7edfc9b7b2018
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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