HCID 10457822, compound → HCID 10480338, compound

HRID 425933Notes

Reaction equation

HRID 425933 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-1e8adfe68fa249adb2e857e5bb0147df
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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