Cyclohexene → HCID 54740910, compound

HRID 553551Notes

Reaction equation

HRID 553551 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])=[C:10]3[OH:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C1CCCCC=1.OC1C2C(=NC=C(I)C=2)N(C)C(=O)C=1C(=O)CCC(O)=O>[Pd]>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[N:13]([CH3:17])[C:12](=[O:18])[C:11]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:10]3[OH:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 57742965HCID 57742965, compoundHCID 67407936HCID 67407936, compound

Product 1

HCID 54740910HCID 54740910, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Methyl 4-(6-cyclohexenyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)-4-oxobutanoate. The title compound is prepared by Palladium mediated Heck cross coupling reaction of cyclohexene and methyl 4-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)-4-oxobutanoate (Method 4) according to the procedure set forth in Heck, R. F.; Nolley, J. P. J. Org. Chem., 37, 2320-22 (1971).

Sources & evidence

ORD record
ord-746074a2a9224697b8cd13056de0796e
Source dataset
uspto-grants-2011_11
Patent number
US08048894B2

Reaction notes

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