7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one → 7-[(1-tert-butylpiperidin-4-ylidene)methyl]-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394184Notes

Reaction equation

HRID 394184 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:29]([N:33]1[CH2:38][CH2:37][C:36](=[CH:39][Sn](C)(C)C)[CH2:35][CH2:34]1)([CH3:32])([CH3:31])[CH3:30]>>[C:29]([N:33]1[CH2:38][CH2:37][C:36](=[CH:39][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]3[C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])=[C:4]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[Cl:28])[N:3]=2)[CH2:35][CH2:34]1)([CH3:32])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 226479107-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-oneHCID 226479361-Tert-butyl-4-[(trimethylstannyl)methylene]piperidine

Product 1

HCID 226481727-[(1-tert-butylpiperidin-4-ylidene)methyl]-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

Procedure

The 7-[(1-tert-butylpiperidin-4-ylidene)methyl]-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one was prepared from 7-bromo-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND CCC1) and 1-tert-butyl-4-[(trimethylstannyl)methylene]piperidine (INTERMEDIATE ABA3) by a procedure analogous to that described in EXAMPLE CZC1. Mass spectrum (ESI) 570 (M+1).

Sources & evidence

ORD record
ord-9a5097f01b69493cb7d55fa8b5c1f458
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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