HCID 10457822, compound → HCID 10480338, compound

HRID 1766755Notes

Reaction equation

HRID 1766755 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:28])=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[C:15]3[C:21]2[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH:26]=2)[CH:11]=1>CO.C(O)(=O)C.C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:28])=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[C:15]3[CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[CH:11]=1

Participants

6

Reactant 1

HCID 10457822HCID 10457822, compound

Product 1

HCID 10480338HCID 10480338, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a de-gassed solution of 3-(2,6-dichloro-benzyloxy)-5-[3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-pyridin-2-ylamine (example I-61, 130 mg, 0.27 mmol) in methanol (50 mL) and acetic acid (5 mL) was added 10% Pd/C (50 mg). The solution was degassed and charged with hydrogen for three times, and then was stirred under hydrogen balloon-for over night. The mixture was filtered through a celite pad, washed with methanol, and then condensed. The residue was dissolved in ethyl acetate, washed with sat. NaHCO3 and brine, dried over Na2SO4, and condensed. The crude product was purified on a silica gel column eluting with dichloromethane-methanol-triethyl amine (95:5:0.1) to provide 3-(2,6-dichloro-benzyloxy)-5-[3-(1-methyl-piperidin-4-yl)-1H-indol-5-yl]-pyridin-2-ylamine as a white solid.

Workup

  1. customThe solution was degassed
  2. additioncharged with hydrogen for three times
  3. filtrationThe mixture was filtered through a celite pad
  4. washwashed with methanol
  5. customcondensed
  6. washwashed with sat. NaHCO3 and brine
  7. dry with materialdried over Na2SO4, and condensed
  8. customThe crude product was purified on a silica gel column
  9. washeluting with dichloromethane-methanol-triethyl amine (95:5:0.1)

Sources & evidence

ORD record
ord-ebf2d0e771384c5b82e3afcdbf9d394a
Source dataset
uspto-grants-2007_06
Patent number
US07230098B2

Reaction notes

Loading…