Triphenylphosphine → HCID 10050399, compound

HRID 902026Notes

Reaction equation

HRID 902026 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]2[N:14]=[C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[C:16]([C:17]3[C:26]4[C:21](=[CH:22][C:23](Br)=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[C:10]2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]([O-:56])(=[O:55])C.[Na+].[C]=O>CN(C=O)C.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:34][O:56][C:53]([C:23]1[CH:22]=[C:21]2[C:26]([C:17]([C:16]3[C:15]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[N:14][N:11]4[CH:12]=[CH:13][C:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[CH:9][C:10]=34)=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1)=[O:55]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 517045Sodium AcetateHCID 69222812HCID 69222812, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 10050399HCID 10050399, compoundYield 255%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(5-benzyl-2-pyridin-2-yl-pyrazolo-[1,5-a]-pyridin-3-yl)-7-bromo-quinoline (118 mg, 0.24 mmol) in DMF (4 mL) and methanol (4 mL), add triphenylphosphine (20 mg, 0.07 mmol) and sodium acetate (28 mg, 0.36 mmol). Bubble nitrogen for 10 minutes. Add palladium acetate (16 mg, 0.07 mmol) and bubble nitrogen for another 10 minutes. Bubble carbon monoxide through the solution for 5 minutes and attach a carbon monoxide balloon. Heat the reaction mixture at 80° C. for 2 days. Cool the reaction mixture to room temperature. Add water (20 mL) and extract the aqueous solution with ethyl acetate (3×20 mL). Dry the combined organic layers with sodium sulfate and concentrate. Purify by flash column chromatography (SiO2, 20-50% ethyl acetate/hexanes) to give the title compound 84 mg (75%) as a yellow solid.

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. extractionAdd water (20 mL) and extract the aqueous solution with ethyl acetate (3×20 mL)
  3. dry with materialDry the combined organic layers with sodium sulfate
  4. concentrationconcentrate
  5. customPurify by flash column chromatography (SiO2, 20-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f71ec513810646159adbbc8398130dc4
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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