2-(4-(4-Ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetic acid → 2-(4-(4-Ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetic acid

HRID 1050145Notes

Reaction equation

HRID 1050145 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([O:10]CC2C=CC(OC)=CC=2)[N:7]=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[C:22]([F:30])[CH:21]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]1[C:5]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([OH:29])=[O:28])=[C:22]([F:30])[CH:21]=2)=[CH:6][NH:7][C:8](=[O:10])[CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 904227052-(4-(4-Ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetic acid

Product 1

HCID 904228612-(4-(4-Ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetic acidYield 113%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(4-(4-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetic acid (0.5 g, 1.215 mmol) in MeOH (10 mL) stirred under nitrogen at 20° C. was added Pd/C (0.013 g, 0.122 mmol) in one charge. The reaction mixture was reacted with a H2 balloon at 20° C. for 12 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give the crude 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetic acid (0.4 g, 1.373 mmol). TLC (DCM/MeOH=10:1, Rf=0.2): 1H NMR (400 MHz, DMSO-d6) δ 7.32-7.15 (m, 4H), 5.78 (s, 1H), 4.01-4.00 (m, 2H), 3.59 (s, 2H), 1.26-1.23 (m, 3H); ES-LCMS m/z 292 (M+H).

Workup

  1. additioncharge
  2. customThe reaction mixture was reacted with a H2 balloon at 20° C. for 12 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-935a4f9afa004d2c9fead6ee237e6b66
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

Loading…