Potassium Carbonate → 7-(1,2-dimethyl-1H-imidazol-5-yl)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79360

Reaction equation

HRID 79360 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH2:31][CH3:32])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[CH3:49][N:50]1[CH:54]=[CH:53][N:52]=[C:51]1[CH3:55].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:49][N:50]1[C:54]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]([C:11]([NH:13][C:14]4[CH:22]=[CH:21][CH:20]=[C:19]5[C:15]=4[C:16]([CH2:31][CH3:32])=[N:17][N:18]5[CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[O:12])=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:53][N:52]=[C:51]1[CH3:55]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 156171,2-DimethylimidazoleHCID 521585Tris(furan-2-yl)phosphaneHCID 672595577-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 672601647-(1,2-dimethyl-1H-imidazol-5-yl)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 15%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To 7-bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl) imidazo[1,2-a]pyridine-3-carboxamide (prepared as in Example 127, Step A; 129 mg, 0.264 mmol) in DMF (4 mL) was added trifuran-2-ylphosphine (12.2 mg, 0.0527 mmol), 1,2-dimethyl-1H-imidazole (50.7 mg, 0.527 mmol), palladium diacetate (5.92 mg, 0.0264 mmol) and K2CO3 (72.9 mg, 0.527 mmol). The reaction mixture was purged with argon, sealed and heated to 140° C. for 3 hours. The mixture was cooled to ambient temperature, diluted with DCM (20 mL) and washed with H2O. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH, 10:1:0.1) to provide the final product (20 mg). MS (ES+APCI) m/z=505 (M+H).

Workup

  1. customThe reaction mixture was purged with argon
  2. customsealed
  3. temperatureThe mixture was cooled to ambient temperature
  4. additiondiluted with DCM (20 mL)
  5. washwashed with H2O
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH, 10:1:0.1)

Sources & evidence

ORD record
ord-cdaf755798a4457789dfc84e337d2c2f
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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