2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 86718104, compound

HRID 2205102Notes

Reaction equation

Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH3:22]C(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[Al](C)(C)C>O1CCOCC1.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]>[CH3:22][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (100 mg, 0.34 mmol, 1.00 equiv), Pd2(dba)3 (12 mg, 0.01 mmol, 0.04 equiv), x-phos (6 mg, 0.01 mmol, 0.04 equiv), and Al(CH3)3 (0.5 mL, 3.00 equiv, 2.5M) in 1,4-dioxane (3 mL) was placed in a 10-mL sealed tube under an inert atmosphere allowed to react, with stirring, for 6 hr while the temperature was maintained at 100° C. in an oil bath. The reaction progress was monitored by TLC (ethyl acetate:petroleum ether (1:1)). The resulting mixture was concentrated under vacuum. The residue was purified via silica gel column (ethyl acetate/petroleum ether (1:20)) yielding 60 mg (64%) of methyl 3-methyl-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

customsealed tube under an inert atmosphere
customto react
concentrationThe resulting mixture was concentrated under vacuum
customThe residue was purified via silica gel column (ethyl acetate/petroleum ether (1:20))

Sources & evidence

ORD record: ord-14f04f73e0144ed48a1b779626e2d850
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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