Hydrochloric Acid → HCID 89704722, compound

HRID 1481350Notes

Reaction equation

HRID 1481350 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.C[O:12][C:13](=O)[CH:14]=[CH2:15].CC([O-:21])(C)C.[K+].Cl.[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>>[CH3:26][O:27][C:28]([CH:24]1[CH2:25][C:8]([C:9]#[N:10])([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:15][CH2:14][C:13]1=[O:12])=[O:21]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 14751282-(6-Chloropyridin-3-yl)acetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 89704722HCID 89704722, compound

Procedure

To a solution of 2-(6-chloro-3-pyridinyl)-acetonitrile (13.1 mmol) in 35 mL THF were added methylacrylate (26.2 mmol) and KOtBu (15.7 mmol). The reaction mixture was stirred at RT for 1 h. The mixture was acidified with 1N HCl solution and then extracted twice with DCM. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept/EtOAc (90/10 to 50/50) gives the desired compound as white solid.

Workup

  1. extractionextracted twice with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-de704d6bf3cc45398975dc223b54df05
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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