Phenylboronic Acid → HCID 54740912, compound

HRID 553550Notes

Reaction equation

HRID 553550 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=C[CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=2)[N:5]([CH3:18])[C:4](=[O:19])[C:3]=1[C:20](=[O:27])[CH2:21][CH2:22][C:23]([O:25]C)=[O:24].C1(B(O)O)C=CC=CC=1.OC1C2C(=NC=C(I)C=2)[N:41](C)C(=O)C=1C(=O)CCC(O)=O.C([Sn](CCCC)(CCCC)C1C=CC=CC=1)CCC.OC1C2C(=NC=C(I)C=2)N(C)C(=O)C=1C(=O)CCC(OC)=O>[Pd]>[OH:1][C:2]1[C:11]2[C:6](=[N:41][CH:8]=[C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:10]=2)[N:5]([CH3:18])[C:4](=[O:19])[C:3]=1[C:20](=[O:27])[CH2:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

7

Reactant 5

HCID 66827Phenylboronic AcidHCID 607632TributylphenyltinHCID 57742965HCID 57742965, compoundHCID 67406545HCID 67406545, compoundHCID 67406879HCID 67406879, compound

Product 1

HCID 54740912HCID 54740912, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

Methyl 4-(4-hydroxy-1-methyl-2-oxo-6-phenyl-1,2-dihydroquinolin-3-yl)-4-oxobutanoate. The title compound is prepared by Palladium mediated Suzuki cross coupling reaction of phenyl boronic acid 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 Miyaura, N.; Suzuki, A. Chem. Rev., 95, 2457-83 (1995). Alternatively, the title compound is prepared by Palladium mediated Stille cross coupling reaction of tributyl(phenyl)stannane and methyl 4-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)-4-oxobutanoate according to the procedure set forth in Stille, J. K. Agnew. Chem. Int. Ed. Engl., 25, 508-24 (1986).

Sources & evidence

ORD record
ord-4bb5091b3f8746e685eb3a07f4581ed1
Source dataset
uspto-grants-2011_11
Patent number
US08048894B2

Reaction notes

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