Triethylamine → HCID 86699336, compound

HRID 706641Notes

Reaction equation

HRID 706641 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]([CH3:31])=[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.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.C([Sn](CCCC)(CCCC)[C:59]([O:61][CH2:62][CH3:63])=[CH2:60])CCC.C(N(CC)CC)C>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]>[CH2:62]([O:61][C:59]([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]([CH3:31])=[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)=[CH2:60])[CH3:63]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 679764107-bromo-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 86699336HCID 86699336, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A flask equipped with a reflux condenser and a nitrogen line was charged with 7-bromo-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (Example 50, Steps A-B; 74.8 mg, 0.157 mmol), tri-O-tolylphosphine (9.6 mg, 0.031 mmol), and tris(dibenzylideneacetone)dipalladium (0) (14.4 mg, 0.015 mmol) Anhydrous DMF (2 mL), tributyl(1-ethoxyvinyl)tin (0.07 mL, 0.22 mmol) and triethylamine (0.03 mL, 0.22 mmol) were added to the flask, and the reaction mixture was degassed under nitrogen and stirred at 100° C. for 6 hours. The reaction mixture was cooled, diluted with excess water and extracted with DCM and EtOAc. The combined organics were dried over anhydrous sodium sulfate and concentrated. The crude product was purified by preparative thin-layer chromatography (silica, 5% MeOH/DCM as eluent) to afford 56.4 mg of desired product as a yellow solid.

Workup

  1. customA flask equipped with a reflux condenser
  2. additionwere added to the flask
  3. customthe reaction mixture was degassed under nitrogen
  4. temperatureThe reaction mixture was cooled
  5. additiondiluted with excess water
  6. extractionextracted with DCM and EtOAc
  7. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by preparative thin-layer chromatography (silica, 5% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-e8f4d70b99d144c5b0118d14bc58ed80
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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