HCID 12189039, compound → HCID 10559756, compound

HRID 712474Notes

Reaction equation

HRID 712474 reaction equation
C([O:8][C:9]1[C:10](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:10]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 12189039HCID 12189039, compound

Product 1

HCID 10559756HCID 10559756, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-ethyl 3-(3-(benzyloxy)pyridin-2-yl)acrylate (3.00 g) in MeOH was added a catalytic amount of 10% Pd/C. The reaction mixture was stirred for 2 h at room temperature under H2 and filtered. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (1.34 g, 65.00%), and the crude product was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 196.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 9.41 (bs, 1H), 8.15-8.21 (m, 1H), 7.3-7.0 (m, 2H), 4.15-4.05 (m, 2H), 3.15 (t, J=4.2 Hz, 2H), 2.85 (t, J=8.0 Hz, 2H), 1.2 (t, J=4.2 Hz, 2H) ppm.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-551655f84b7242f6a4d5930f13d96977
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

Loading…