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

HRID 1876856Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.00 g, 0.0103 mol) in acetonitrile (30 mL) was added 3-cyclopentylacrylonitrile (1.25 g, 0.0103 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (1.54 mL, 0.0103 mol). The resulting mixture was stirred at 60° C. overnight, then evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 50% EtOAc in hexanes, to give the desired product (2.36 g, 73%). LCMS (M+H) 316.1.

Workup

customevaporated to dryness
customThe residue was purified on silica gel
washeluting with 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record: ord-770ec1bcb2e4427487c5681d3b64aaf4
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309718B2

Reaction notes

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