1-Tert-butyl-4-(trimethylstannyl)-1,2,3,6-tetrahydropyridine → 8-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-chloro-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one

HRID 1360675Notes

Reaction equation

HRID 1360675 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:21])[N:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19])[C:8](=[O:20])[CH:7]=[CH:6]2.[C:22]([N:26]1[CH2:31][CH:30]=[C:29]([Sn](C)(C)C)[CH2:28][CH2:27]1)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([N:26]1[CH2:27][CH:28]=[C:29]([C:2]2[CH:3]=[C:4]([Cl:21])[N:5]3[C:10]([CH:11]=2)=[C:9]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[C:8](=[O:20])[CH:7]=[CH:6]3)[CH2:30][CH2:31]1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 226481771-Tert-butyl-4-(trimethylstannyl)-1,2,3,6-tetrahydropyridineHCID 577003748-bromo-6-chloro-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one

Product 1

HCID 577003708-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-chloro-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-bromo-6-chloro-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one (Example 17, 132 mg) in THF was added 1-t-butyl-4-(trimethylstannyl)-1,2,3,6-tetrahydropyridine (process route disclosed in U.S. Pat. No. 6,809,199, 90 mg.), dichlorobis(triphenylphosphine) palladium (21 mg) and heated to reflux for 12 h. The mixture was concentrated and purified by silica gel (methylene chloride/acetone=1/2) to give title compound (57 mg).

Workup

  1. temperatureto reflux for 12 h
  2. concentrationThe mixture was concentrated
  3. custompurified by silica gel (methylene chloride/acetone=1/2)

Sources & evidence

ORD record
ord-5eaf009c2e664ec299f0296a1e2417a7
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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