1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69033688, compound

HRID 1876874Notes

Reaction equation

HRID 1876874 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.[Si:15]([O:22][CH:23]1[CH2:28][CH2:27][C:26](=[CH:29][C:30]#[N:31])[CH2:25][CH2:24]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N12CCCN=C1CCCCC2>C(#N)C>[Si:15]([O:22][CH:23]1[CH2:24][CH2:25][C:26]([CH2:29][C:30]#[N:31])([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)[CH2:27][CH2:28]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

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 68733627HCID 68733627, compound

Product 1

HCID 69033688HCID 69033688, compound

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 (3.09 g, 0.0159 mol) in acetonitrile (39.8 mL) was added (4-(tert-butyl(dimethyl)silyl)oxycyclohexylidene)acetonitrile (4.80 g, 0.0191 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (1.19 mL, 0.00797 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 20% EtOAc in hexanes, to give the desired product as cis- and trans-mixture (2.33 g, 33%). LCMS (M+H) 446.3.

Workup

  1. customevaporated to dryness
  2. customThe mixture was purified on silica gel
  3. washeluting with 0 to 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-92aa8aa0f94847fc82cf3d3edd80c585
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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