4-Cyanopyridine → HCID 86634789, compound

HRID 911087Notes

Reaction equation

HRID 911087 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C[Si](C)(C)[CH2:11][CH2:12][OH:13].[H-].[Na+].ClC1[CH:26]=[N:25][CH:24]=[CH:23]C=1C#N.[Cl-:27].[NH4+]>C1COCC1>[Cl:27][C:4]1[C:3]([O:13][C:12]2[CH:23]=[CH:24][N:25]=[CH:26][CH:11]=2)=[C:2]([CH:7]=[CH:6][N:5]=1)[C:1]#[N:8]

Participants

7

Reactant 5

HCID 75064-CyanopyridineHCID 180132-(Trimethylsilyl)ethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 106783063-Chloropyridine-4-carbonitrile

Product 1

HCID 86634789HCID 86634789, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation of 32-(trimethylsilyl)ethoxy)isonicotinonitrile: A flask was charged with 2-(trimethylsilyl)ethanol (1.02 g, 8.66 mmol) and added THF (20 mL). Sodium hydride (0.219 g, 8.66 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. 3-Chloroisonicotinonitrile (1.00 g, 7.22 mmol) was added, and the reaction mixture was stirred at ambient temperature for 1 hour and then at 50° C. overnight. A saturated solution of ammonium chloride was added. The reaction mixture was extracted with ethyl acetate, dried and concentrated to give the desired product (1.30 g, 81.7% yield) as light brown semi solid material.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 1 hour
  2. customat 50° C.
  3. customovernight
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b63e090e52264d9d83fa307a0c372d0b
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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