Toluene → HCID 66678632, compound

HRID 902033Notes

Reaction equation

HRID 902033 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[C:13]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:14][N:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=34)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:50]([O:54][CH3:55])(=[O:53])[CH:51]=[CH2:52].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:55][O:54][C:50](=[O:53])[CH:51]=[CH:52][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[C:13]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=4)=[N:14][N:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=34)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 69221493HCID 69221493, compound

Product 1

HCID 66678632HCID 66678632, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Combine 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (0.15 g, 0.36 mmol), tri-o-tolylphosphine (0.38 g, 1.26 mmol), tribuytlamine (0.12 mL, 0.5 mmol), methyl acrylate (0.065 ml, 0.72 mmol), anhydrous toluene (3 mL), and DMF (1.5 mL). Bubble nitrogen gas through the solution for 20 minutes. Add palladium acetate (4.0 mg, 0.018 mmol). Heat the reaction mixture at 80° C. for 48 hours. Chromatograph the residue on silica gel (elute with 2% methanol/methylene chloride, then 4% methanol/methylene chloride). Further purification by preparative HPLC affords the title compound 42 mg (28%) as a yellowish solid.

Workup

  1. washChromatograph the residue on silica gel (elute with 2% methanol/methylene chloride
  2. customFurther purification by preparative HPLC

Sources & evidence

ORD record
ord-edb15cfb686349baadb56c42d21fb4ea
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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