Piperidine → HCID 44539730, compound

HRID 1616034Notes

Reaction equation

HRID 1616034 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])=[N:6][CH:7]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CS(C)=O.CO>[NH:24]1[C:25]2[C:21](=[C:20]([C:18]3[CH:17]=[C:16]4[C:12]([CH:13]=[N:14][NH:15]4)=[C:11]([NH:10][C:8]([C:5]4[CH:4]=[CH:3][C:2]([N:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:7][N:6]=4)=[O:9])[CH:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 44540317HCID 44540317, compound

Product 1

HCID 44539730HCID 44539730, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 22036561Dimethyl sulfoxide methanolSolvent

Conditions

Temperature
150 °C

Procedure

5-Bromo-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (50 mg, 0.12 mmol) and piperidine (1 ml, 10.1 mmol) were placed in a microwave vial. Pd2dba3 (5 mg, 0.006 mmol), BINAP (7.2 mg, 0.012 mmol) and cesium carbonate (57 mg, 0.17 mmol) were added and the mixture was heated at 150° C. for 75 mins under microwave irradiation. The reaction mixture was concentrated in vacuo to give a crude residue that was suspended in 1:1 DMSO/MeOH (1 ml) and filtered to give an orange solution that was purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1 g aminopropyl column, eluted with MeOH and the solvent removed under a stream of nitrogen to give the title compound (18 mg) as a yellow gum.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a crude residue that
  3. filtrationfiltered
  4. customto give an orange solution that
  5. customwas purified by Mass Directed Automated Preparative HPLC (Method C)
  6. washeluted with MeOH
  7. customthe solvent removed under a stream of nitrogen

Sources & evidence

ORD record
ord-7d1322573fd546b7a02f9cb439e4feef
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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