3-[5-Chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-acrylic acid ethyl ester → 3-[5-Chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-propionic acid ethyl ester

HRID 2387118Notes

Reaction equation

HRID 2387118 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[CH:6][C:7]1[CH:8]=[N:9][C:10]([C:14]([C:17]#[N:18])([CH3:16])[CH3:15])=[C:11]([Cl:13])[CH:12]=1)[CH3:2].[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:14]([C:17]#[N:18])([CH3:15])[CH3:16])=[C:11]([Cl:13])[CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 670843503-[5-Chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-acrylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 587640323-[5-Chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-[5-chloro-6-(cyano-dimethyl-methyl)-pyridin-3-yl]-acrylic acid ethyl ester (0.74 g, 2.65 mmol) from step 3 above was added ethanol (10 mL) and Pd(OH)2/C (0.37 g). The reaction was placed under a hydrogen atmosphere using a balloon filled with hydrogen. The slurry was stirred vigorously for 1 hour. The reaction was filtered to remove all of the solids, and the liquid was concentrated to an white solid which was used in next reaction without further purification. 1H NMR (400 MHz, CDCl3): δ 1.25 (t, J=7.7 Hz, 3 H), 1.85 (s, 6 H), 2.62-2.66 (m, 2 H), 2.92-2.98 (m, 2H), 4.15 (q, J=14, 7.7 Hz, 2 H), 7.61 (d, J=2 Hz, 1 H), 8.3 (d, J=2 Hz, 1 H). ESIMS (MH+): 289.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove all of the solids
  3. concentrationthe liquid was concentrated to an white solid which
  4. customwas used in next reaction without further purification

Sources & evidence

ORD record
ord-f88d5cf2b98a4b208e3ec26f2a48a209
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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