Cyclopentylideneacetonitrile → HCID 59402390, compound

HRID 2090292Notes

Reaction equation

HRID 2090292 reaction equation
[C:1]1(=[CH:6][C:7]#[N:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1([CH3:22])[C:14]([CH3:16])([CH3:15])[O:13][B:12]([C:17]2[CH:18]=[N:19][NH:20][CH:21]=2)[O:11]1.N12CCCN=C1CCCCC2>C(#N)C>[CH3:9][C:10]1([CH3:22])[C:14]([CH3:15])([CH3:16])[O:13][B:12]([C:17]2[CH:21]=[N:20][N:19]([C:1]3([CH2:6][C:7]#[N:8])[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:18]=2)[O:11]1

Participants

5

Reactant 3

HCID 79810CyclopentylideneacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 59402390HCID 59402390, compoundYield 17.29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of cyclopentylideneacetonitrile (0.65 g, 0.0061 mol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.60 g, 0.0031 mol, Aldrich, Cat. 525057), and 1,8-diazabicyclo[5.4.0]undec-7-ene (47 mg, 0.00031 mol, Aldrich, Cat. No. 139009) in acetonitrile (7 mL) was stirred at 60° C. overnight. After cooling to r.t., the reaction mixture was concentrated. The crude residue was purified by flash column chromatography on a silica gel column using 40% ethyl acetate in hexane as eluent to afford the desired compound (161 mg, 17.29%). LCMS (M+H)+: m/z=302.4.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe crude residue was purified by flash column chromatography on a silica gel column

Sources & evidence

ORD record
ord-f0aac97223f548b8bb9e4d042f09c218
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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