HCID 67070107, compound → HCID 67070164, compound

HRID 2390841Notes

Reaction equation

HRID 2390841 reaction equation
[C:1]([C:5]1[C:6]([O:28][CH3:29])=[C:7]([C:19]#[C:20][C:21]2[N:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[OH-].[OH-].[Pd+2].CCOC(C)=O.CO>[C:1]([C:5]1[C:6]([O:28][CH3:29])=[C:7]([CH2:19][CH2:20][C:21]2[N:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67070107HCID 67070107, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67070164HCID 67070164, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

step 2—A suspension of 180 (0.322 g, 0.831 mmol) 20% Pd(OH)2/C (0.146 g) and EtOAc/MeOH (1:1, 40 mL) was hydrogenated in a Parr Shaker under 50 psi of hydrogen for 2 h. The resulting suspension was filtered through CELITE and evaporated. The crude product was purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (0 to 90% EtOAc) to afford 0.183 g of 6-{2-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-ethyl}-pyridin-3-ylamine (182) as a yellow foam.

Workup

  1. filtrationThe resulting suspension was filtered through CELITE
  2. customevaporated
  3. customThe crude product was purified by SiO2 chromatography
  4. washeluting with a EtOAc/hexane gradient (0 to 90% EtOAc)

Sources & evidence

ORD record
ord-8b83fdade2614070b6a3c7490f091f3e
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…