2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 86718131, compound

HRID 2205146Notes

Reaction equation

Br[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][CH:23](C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[Zn](CC)CC>C1COCC1.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]>[CH2:22]([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)[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (100 mg, 0.29 mmol, 1.00 equiv), X-phos (14 mg, 0.03 mmol, 0.10 equiv), Pd2(dba)3 (27 mg, 0.03 mmol, 0.10 equiv) in THF (10 mL), and Et2Zn in THF (5.8 mL, 20.00 equiv, 1M was allowed to react, with stifling, overnight while the temperature was maintained at 80° C. in an oil bath. The reaction was quenched by the addition of 2 mL of water. The resulting mixture was concentrated under vacuum and purified by prep-TLC (petroleum ether:ethyl acetate (4:1)) yielding 50 mg (35%) of methyl 3-ethyl-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

customto react, with stifling, overnight while the temperature
customThe reaction was quenched by the addition of 2 mL of water
concentrationThe resulting mixture was concentrated under vacuum
custompurified by prep-TLC (petroleum ether:ethyl acetate (4:1))

Sources & evidence

ORD record: ord-230cab76b1c04984beca050dc25c4dcf
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09370522B2

Reaction notes

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