Triphenylphosphine → HCID 59700621, compound

HRID 902025Notes

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.[C:28]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:47]([O-:50])(=[O:49])C.[Na+].[C]=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C.CO>[CH3:28][O:50][C:47]([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)=[O:49]

Participants

Conditions

Temperature: 80 °C

Procedure

Combine 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (0.18 g, 0.43 mmol), triphenylphosphine (36 mg, 0.14 mmol), sodium acetate (0.05 g, 0.61 mmol), methanol (2.7 mL), and DMF (2.7 mL). Bubble nitrogen gas through the solution for 10 minutes. Add palladium acetate (0.03 g, 0.13 mmol). Bubble nitrogen gas through the solution for another 10 minutes. Connect a carbon monoxide balloon to the reaction vessel and heat at 80° C. for 24 hours. Evaporate the solvent in vacuo. Chromatograph the residue on silica gel (elute with 50% ethyl acetate/hexanes then 75% ethyl acetate/hexanes) to afford the title compound 72 mg (42%) as a yellowish solid.

Workup

waitBubble nitrogen gas through the solution for another 10 minutes
customEvaporate the solvent in vacuo
washChromatograph the residue on silica gel (elute with 50% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-1042b126e0784c9b9eeea843866ce9c8
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365066B2

Reaction notes

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