2-Methylpyrrolidine → 1-[2-(6-Bromo-naphthalen-2-yl)-ethyl]-2-methyl-pyrrolidine

HRID 857530Notes

Reaction equation

HRID 857530 reaction equation
N1NC(=O)C=CC=1.BrC1C=C2C(=CC=1)C=C(OS(C(F)(F)F)(=O)=O)C=C2.[Br:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH:38]=[CH2:39])[CH:34]=2)[CH:29]=1.[CH3:40][CH:41]1[CH2:45][CH2:44][CH2:43][NH:42]1.C([Li])CCC>>[Br:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH:34]=[C:33]([CH2:38][CH2:39][N:42]1[CH2:43][CH2:44][CH2:45][CH:41]1[CH3:40])[CH:32]=[CH:31]2

Participants

6

Reactant 5

HCID 130032-MethylpyrrolidineHCID 681533(2H)-PyridazinoneHCID 115648892-Bromo-6-ethenylnaphthalene2×HCID 153112166-Bromo-2-naphthyl TrifluoromethanesulfonateHCID 178418339Butyllithium

Product 1

HCID 115225881-[2-(6-Bromo-naphthalen-2-yl)-ethyl]-2-methyl-pyrrolidine

Procedure

Another aspect of the invention, relates to the preparation of 2-(6-{2-methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one active agent. The process comprises the steps of converting a trifluoro-methanesulfonic acid 6-bromo-naphthalen-2-yl ester to 2-bromo-6-vinyl-naphthalene; and reacting 2-bromo-6-vinyl-naphthalene with a 2-methylpyrrolidine anion generated with n-butyllithium to provide a 1-[2-(6-bromo-naphthalen-2-yl)-ethyl]-2-methyl-pyrrolidine compound, which is reacted with 2H-pyridazin-3-one in the presence of a copper catalyst and ligand to provide a 2-(6-{2-methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one active agent.

Sources & evidence

ORD record
ord-c52df8fd7b5a4f91828e9309df974511
Source dataset
uspto-grants-2006_12
Patent number
US07145005B2

Reaction notes

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