1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(Cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)cyclobutane-1-carbonitrile

HRID 1876881Notes

Reaction equation

HRID 1876881 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:15]([CH:17]=[C:18]1[CH2:21][CH:20]([C:22]#[N:23])[CH2:19]1)#[N:16].N12CCCN=C1CCCCC2>C(#N)C>[C:15]([CH2:17][C:18]1([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)[CH2:21][CH:20]([C:22]#[N:23])[CH2:19]1)#[N:16]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 66824380HCID 66824380, compound

Product 1

HCID 687563623-(Cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)cyclobutane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.73 g, 0.00890 mol) in acetonitrile (22.2 mL) was added 3-(cyanomethylene)cyclobutanecarbonitrile (1.05 g, 0.00889 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.666 mL, 0.00445 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 racemic mixture (320 mg, 11.5%). LCMS (M+H) 313.4.

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-c996529aa388461087dc7c9b10eba54f
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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