Sodium Carbonate → N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-6-methyl-2-pyridinecarboxamide

HRID 1616048Notes

Reaction equation

HRID 1616048 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)=[O:14])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1[CH2:33][CH2:32]OCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:7]1[C:32]2[C:33](=[C:10]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][N:8]4[CH3:11])=[C:4]([NH:12][C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=4)=[O:14])[CH:3]=3)[CH:2]=[CH:3][CH:4]=2)[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 58268015HCID 58268015, compound

Product 1

HCID 44540227N-[6-(1H-Indol-4-yl)-1-methyl-1H-indazol-4-yl]-6-methyl-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

A mixture of N-(6-bromo-1-methyl-1H-indazol-4-yl)-6-methyl-2-pyridinecarboxamide (50 mg, 0.14 mmol), indole-4-boranepinacoloate ester (40 mg, 0.18 mmol, commercially available), Pd(dppf)Cl2 (22 mg, 0.03 mmol) and sodium carbonate (2M aqueous, 0.26 ml) in 1,4-dioxane (2 ml) was heated to 150° C. under microwave conditions for 10 minutes. The mixture was extracted with dichloromethane (2×15 ml) and concentrated in vacuo and the residue was purified by HPLC (Method B) to afford the title compound (23 mg).

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×15 ml)
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by HPLC (Method B)

Sources & evidence

ORD record
ord-2acb486ef059418a9844bf49d0b37613
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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