7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one → Tert-butyl 3-[5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate
Reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[Cl:28])[N:3]=1.C[Sn](C)(C)[C:31]1[CH2:37][CH:36]2[N:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:33]([CH2:34][CH2:35]2)[CH:32]=1>>[Cl:28][C:22]1[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=1[C:4]1[N:3]=[C:2]([C:31]2[CH2:32][CH:33]3[N:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:36]([CH2:35][CH2:34]3)[CH:37]=2)[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19]Participants
3
Reactant 2
Product 1
Procedure
The tert-butyl 3-[5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate was prepared from 7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND CCC1) and tert-butyl 3-(trimethylstannyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (COMPOUND PPA-3) by a procedure analogous to that described in EXAMPLE CZC1, except that the eluting solvents in the purification step were 20:80 acetone-hexanes. Mass spectrum (ESI) 626 (M+1).
Sources & evidence
- ORD record
- ord-2f09089681d946dc8ee0ce5e6f8fdbad
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809199B2
Reaction notes
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