Hydrochloric Acid → 5-[4-(4-Methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline dihydrochloride salt
Reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]1[CH:35]=[CH:34][C:19]([CH2:20][CH:21]2[C:30]3[CH:29]=[C:28]4[O:31][CH2:32][O:33][C:27]4=[CH:26][C:25]=3[CH2:24][CH2:23][NH:22]2)=[CH:18][CH:17]=1.[ClH:36].[OH-].[Na+].Cl.CCOCC>>[ClH:36].[ClH:36].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]1[CH:17]=[CH:18][C:19]([CH2:20][CH:21]2[C:30]3[CH:29]=[C:28]4[O:31][CH2:32][O:33][C:27]4=[CH:26][C:25]=3[CH2:24][CH2:23][NH:22]2)=[CH:34][CH:35]=1Participants
5
Reactant 4
Product 1
Procedure
The synthesis of 5-[4-(4-methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline dihydrochloride salt 45 is shown in Scheme-12. Reaction of compound 38 with 4-methoxypyridine-3-boronic acid 19 in the presence of Palladium (II) acetate, triphenylphosphine, and Na2CO3 in anhydrous 2-propanol yielded 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 43 which was treated with trifluoroacetic acid in dichloromethane to get 5-[4-(4-methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline trifluoro acetate salt 44. Compound 44 was treated by 37% HCl, 1N NaOH followed by 2M HCl/Ether in MeOH-Ether to obtain 45.
Sources & evidence
- ORD record
- ord-e5cb60f009144d949d07281560220ac9
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507523B2
Reaction notes
Loading…