Sodium Carbonate → HCID 86679169, compound

HRID 1774816Notes

Reaction equation

HRID 1774816 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([CH3:13])([CH3:12])[C:9]([O-:11])=[O:10])[CH:5]=[N:6][CH:7]=1.[K+].[CH3:15][N:16]1[C:25]2[C:20](=[CH:21][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:24]=2)[CH2:19][CH2:18][C:17]1=[O:35].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:12][C:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[N:16]([CH3:15])[C:17](=[O:35])[CH2:18][CH2:19]3)[CH:3]=1)([CH3:13])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 86679168HCID 86679168, compound

Product 1

HCID 86679169HCID 86679169, compound

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

In analogy to the procedure described for the preparation of example 59 [C], potassium 2-(5-bromopyridin-3-yl)-2-methylpropanoate (example 72 [B]) was reacted with 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) in presence of bis(triphenylphosphine)palladium(II)chloride and Na2CO3 (1M aq. solution) to give the title compound as a brown foam. MS: 325.4 (M+H+).

Sources & evidence

ORD record
ord-032f3545ca2f48388fd6eccfe5b2d057
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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