Nitrogen → tert-Butyl 6-(6-ethoxy-6-oxohex-2-enyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 517878Notes

Reaction equation

[CH2:1]([CH:4]1[N:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:8]2=[N:9][C:10]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[N:12]=[C:7]2[CH2:6][CH2:5]1)[CH:2]=[CH2:3].N#N.[C:37]([O:43][CH2:44][CH3:45])(=[O:42])[CH2:38][CH2:39]C=C>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.[Cu]I>[CH2:44]([O:43][C:37](=[O:42])[CH2:38][CH2:39][CH:3]=[CH:2][CH2:1][CH:4]1[N:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:8]2=[N:9][C:10]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[N:12]=[C:7]2[CH2:6][CH2:5]1)[CH3:45]

Participants

Conditions

Temperature: 40 °C

Procedure

Tert-butyl 6-allyl-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 2)(97 mg, 0.213 mmol) in DCM (3 ml) degassed with N2 was treated with ethyl pent-4-enoate (0.036 ml, 0.255 mmol), copper(I) iodide (4.05 mg, 0.021 mmol) and Grubbs (II) catalyst (9.04 mg, 10.65 μmol). After stirring at 40° C. for 4 hours, the mixture was concentrated under reduced pressure and purification by chromatography on silica eluting with 0-10% EtOAc in iso-hexane afforded the titled compound as a brown oil;

Workup

concentrationthe mixture was concentrated under reduced pressure and purification by chromatography on silica eluting with 0-10% EtOAc in iso-hexane

Sources & evidence

ORD record: ord-bf8fe622fb754beb9351909c429130cc
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115129B2

Reaction notes

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