HCID 86716185, compound → HCID 86716186, compound

HRID 512162Notes

Reaction equation

HRID 512162 reaction equation
[C:1]([C:4]1[N:9]=[CH:8][C:7]([CH:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)[C:11]#[N:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:17][Mg+].[Br-]>C1COCC1>[CH:14]1([CH2:13][CH:10]([C:7]2[CH:8]=[N:9][C:4]([C:1]([OH:3])([CH3:17])[CH3:2])=[CH:5][CH:6]=2)[C:11]#[N:12])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 86716185HCID 86716185, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86716186HCID 86716186, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(6-acetylpyridin-3-yl)-3-cyclopropylpropanenitrile (520 mg, 2.43 mmol) in THF (6 mL) was added MeMgBr (0.89 mL, 2.67 mmol, 3M in Et2O) at 0° C. under N2 and stirred at room temperature for 2 h. The solution was quenched with water and extracted with EtOAc (3×20 mL). The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography on silica gel (EtOAc: Petroleum ether=1:10) to give 3-cyclopropyl-2-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)propanenitrile (200 mg, yield: 35.6%). 1H NMR (CDCl3 varian 400): δ8.41 (d, J=2.4 Hz, 1H), 7.67 (dd, J=8.0 Hz, 2.4 Hz, 1H), 7.36 (dd, J=8.4 Hz, 0.8 Hz,

Workup

  1. customThe solution was quenched with water
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography on silica gel (EtOAc: Petroleum ether=1:10)

Sources & evidence

ORD record
ord-e33cf4c751ff45e5a50983ae7b638c78
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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