HCID 135997589, compound → HCID 135741737, compound

HRID 1678217Notes

Reaction equation

HRID 1678217 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:24]2[NH:25][CH:26]=[CH:27][CH:28]=2)[CH:12]=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[NH:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([C:11]3[CH:10]=[C:9]([OH:8])[CH:14]=[N:13][CH:12]=3)[CH:16]=2)[NH:20][N:19]=1

Participants

4

Reactant 1

HCID 135997589HCID 135997589, compound

Product 1

HCID 135741737HCID 135741737, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(5-benzyloxy-pyridin-3-yl)-3-(1H-pyrrol-2-yl)-1H-indazole (Preparation #16c, E and F (using 5-benzyloxy-3-bromopyridine), 0.015 g, 0.4 mmol) in MeOH (5 mL) and 10 wt. % Pd/C (3 mg) was shaken under an atmosphere of hydrogen (about 40 psi) for about 24 hours. The crude product was filtered and the solvent was removed under reduced pressure to yield 5-[3-(1H-pyrrol-2-yl)-1H-indazol-5-yl]-pyridin-3-ol (0.088 g, 80%); RP-HPLC (Table 1, Method e) Rt=1.78 min; m/z: (M+H)+ 277, (M−H)− 275.

Workup

  1. filtrationThe crude product was filtered
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6346312af9054bdf82fba91c94237e8e
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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