3(2H)-Pyridazinone → 2-(4-(3,4-Dichlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)pyridazin-3(2H)-one

HRID 576107Notes

Reaction equation

HRID 576107 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1.[N:21]1[NH:22][C:23](=[O:27])[CH:24]=[CH:25][CH:26]=1>>[Cl:20][C:15]1[CH:14]=[C:13]([CH:6]2[C:5]3[C:10](=[CH:11][C:2]([N:22]4[C:23](=[O:27])[CH:24]=[CH:25][CH:26]=[N:21]4)=[CH:3][CH:4]=3)[CH2:9][N:8]([CH3:12])[CH2:7]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

3

Reactant 2

HCID 681533(2H)-PyridazinoneHCID 667882077-Bromo-4-(3,4-dichlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 667880342-(4-(3,4-Dichlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)pyridazin-3(2H)-oneYield 23%

Procedure

A procedure similar to the one in Step A of Example 17 was used to couple 7-bromo-4-(3,4-dichlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline with pyridazin-3(2H)-one. 2-(4-(3,4-Dichlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)pyridazin-3(2H)-one was obtained in 23% yield as an off-white foam: ESI MS m/z 386 [M+H]+.

Sources & evidence

ORD record
ord-d9f252e7fa274b408d4364e0c4dc2a47
Source dataset
uspto-grants-2015_05
Patent number
US09034899B2

Reaction notes

Loading…