Stannane, tributyl(1-ethoxyethenyl)- → HCID 86716183, compound

HRID 512160Notes

Reaction equation

HRID 512160 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[C:9]#[N:10])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:20]([O:22][CH2:23][CH3:24])=[CH2:21])CCC>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]1([CH2:11][CH:8]([C:5]2[CH:6]=[N:7][C:2]([C:20]([O:22][CH2:23][CH3:24])=[CH2:21])=[CH:3][CH:4]=2)[C:9]#[N:10])[CH2:14][CH2:13]1

Participants

6

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86716184HCID 86716184, compound

Product 1

HCID 86716183HCID 86716183, compoundYield 169.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-(6-chloropyridin-3-yl)-3-cyclopropylpropanenitrile (1.0 g, 4.86 mmol), tributyl(1-ethoxyvinyl)stannane (3.4 g, 9.72 mmol), Lid (0.612 g, 14.58 mmol) and Pd(PPh3)4 (0.282 mg, 0.243 mmol) in 1,4-dioxane (20 mL) was degassed and heated to 120° C. under N2 overnight. The reaction mixture was diluted with water and extracted with EtOAc (3×30 mL). The combined organic layers were dried over Na2SO4 and concentrated to give 3-cyclopropyl-2-(6-(1-ethoxyvinyl)pyridin-3-yl)propanenitrile (2 g), which was used for the next step without further purification.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-18d4a09f42ad4a17ab4664e3b065f363
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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