HCID 44540226, compound → HCID 44540225, compound

HRID 1616050Notes

Reaction equation

HRID 1616050 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][NH:16]4)=[C:12]([NH:19][C:20]([C:22]4[C:27]([C:28]([CH3:30])=[CH2:29])=[CH:26][CH:25]=[CH:24][N:23]=4)=[O:21])[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>C(O)C.[Pd]>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][NH:16]4)=[C:12]([NH:19][C:20]([C:22]4[C:27]([CH:28]([CH3:30])[CH3:29])=[CH:26][CH:25]=[CH:24][N:23]=4)=[O:21])[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 44540226HCID 44540226, compound

Product 1

HCID 44540225HCID 44540225, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-3-(1-methylethenyl)-2-pyridinecarboxamide (166 mg, 0.42 mmol, prepared as described in Example 62) was dissolved in ethanol and hydrogenated at 25° C. on the H-cube using a 5% palladium on carbon catalyst. The mixture was passed through the flow reactor twice then the catalyst was replaced before the mixture was passed through another two times. The solvent was removed in a stream of nitrogen to give a pale yellow oil. This was purified by mass-directed automated preparative HPLC (Method B) to give the title compound (17 mg) as a white solid.

Workup

  1. customThe solvent was removed in a stream of nitrogen
  2. customto give a pale yellow oil
  3. customThis was purified

Sources & evidence

ORD record
ord-c94b6da2f19d478ea12043ce9fb55737
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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