Hydrochloric Acid → 8-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one hydrochloride

HRID 1360676Notes

Reaction equation

HRID 1360676 reaction equation
[C:1]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:12]=[C:13](Cl)[N:14]3[C:19]([CH:20]=2)=[C:18]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:28])[C:17](=[O:29])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].Cl>COCCOC.C(OCC)(=O)C>[ClH:27].[C:1]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:12]=[C:13]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[Cl:31])[N:14]3[C:19]([CH:20]=2)=[C:18]([C:21]2[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=2[Cl:27])[C:17](=[O:29])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 577003708-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-chloro-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one

Product 1

HCID 160646028-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one hydrochlorideYield 73.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-6-chloro-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one (57 mg) in DME was added 2-chlorophenylboronic acid (38 mg), palladium tetrakis triphenylphosphine (14 mg) and 2N sodium carbonate (0.36 mL). The mixture was heated to 80° C. for a couple of hours, then cooled to room temperature, and diluted with ethyl acetate/saturated aqueous sodium bicarbonate. The organic layers were dried over magnesium sulfate and concentrated. The residue was purified by silica gel (100% acetone). The free base was dissolved in methylene chloride and 3 eq. of HCl (1N in ethyl ether) was added to give the HCl salt (26 mg).

Workup

  1. temperaturecooled to room temperature
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel (100% acetone)
  5. dissolutionThe free base was dissolved in methylene chloride

Sources & evidence

ORD record
ord-99d068d0b43c4c76b9f4d339b694296c
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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