Methanol → methyl 1-benzyl-4-[2-(6-methoxy-1-oxo-3,4-dihydroisoquinolin-2-yl)ethyl]-2-methyl-4H-pyridine-3-carboxylate

HRID 2207157Notes

Reaction equation

HRID 2207157 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:14](=[CH:17][CH2:18][CH3:19])C=O)[CH2:7][CH2:6]2.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:28]([O:34][CH3:35])(=[O:33])[CH2:29][C:30]([CH3:32])=O.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].[CH3:63]O>>[CH2:20]([N:27]1[CH:63]=[CH:19][CH:18]([CH2:17][CH2:14][N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]2=[O:13])[C:29]([C:28]([O:34][CH3:35])=[O:33])=[C:30]1[CH3:32])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 7504BenzylamineHCID 7757Methyl acetoacetateHCID 180504Ceric ammonium nitrateHCID 1317358806-Methoxy-1-oxo-3,4-dihydroisoquinolin-2-ylpent-2-enal

Product 1

HCID 118558013methyl 1-benzyl-4-[2-(6-methoxy-1-oxo-3,4-dihydroisoquinolin-2-yl)ethyl]-2-methyl-4H-pyridine-3-carboxylate

Procedure

The title compound 48 is prepared according to the procedure reported in Example 13 with aldehyde 50 (50 mg, 0.19 mmol), benzylamine (20.6 mg, 1 equiv), methyl acetoacetate (22.4 mg, 1 equiv) and CAN (5.2 mg, 5 mol %) as reactants in MeOH. (Yield 18.9 mg, 21%).

Sources & evidence

ORD record
ord-e5d030d97bc54b9b865c05cf7f487615
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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