Acetonitrile → HCID 68756140, compound

HRID 1876891Notes

Reaction equation

HRID 1876891 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.[O:18]1[CH2:23][CH2:22][CH:21](/[CH:24]=[CH:25]/[C:26]#[N:27])[CH2:20][CH2:19]1.N12CCCN=C1CCCCC2>>[O:18]1[CH2:23][CH2:22][CH:21]([CH:24]([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)[CH2:25][C:26]#[N:27])[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 62390561HCID 62390561, compound

Product 1

HCID 68756140HCID 68756140, compoundYield 60.93%

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.25 g, 0.00644 mol) in acetonitrile (20 mL, 0.4 mol) was added (2E)-3-(tetrahydro-2H-pyran-4-yl)acrylonitrile (1.00 g, 0.00729 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (1.09 mL, 0.00729 mol). The resulting mixture was stirred at room temperature overnight. After being evaporated to dryness, the residue was purified on silica gel, eluting with 0-100% EtOAc in hexanes, to provide the desired product (1.30 g, 60.93%). LCMS (M+H) 332.4.

Workup

  1. customAfter being evaporated to dryness
  2. customthe residue was purified on silica gel
  3. washeluting with 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-f8f6268a29934e1187df90281b11bde8
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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