HCID 22647982, compound → 7-(1-tert-Butyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394144Notes

Reaction equation

HRID 394144 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][CH:24]=[CH:23][C:22]=2[Cl:27])[N:3]=1.[C:28]([N:32]1[CH2:37][CH:36]=[C:35]([Sn](C)(C)C)[CH2:34][CH2:33]1)([CH3:31])([CH3:30])[CH3:29]>O1CCOCC1>[C:28]([N:32]1[CH2:33][CH:34]=[C:35]([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][CH:24]=[CH:23][C:22]=3[Cl:27])[N:3]=2)[CH2:36][CH2:37]1)([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 22647982HCID 22647982, compoundHCID 226481771-Tert-butyl-4-(trimethylstannyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 226478977-(1-tert-Butyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 100 mg of 7-bromo-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND HHH2) and 94 mg of 1-tert-butyl-4-(trimethylstannyl)-1,2,3,6-tetrahydropyridine (COMPOUND PPA-2) in 2 mL of dry dioxane was evacuated and purged three times with Ar. Pd(Ph3P)4 (23 mg) was added and the mixture was evacuated and purged again with Ar. The mixture was heated to reflux and stirred at this temperature overnight, then filtered through Celite and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in MeOH, to yield the title compound. The HCl salt was prepared by dissolving this compound in CH2Cl2, adding 1 eq 1M HCl in Et2O, and concentrating. Mass spectrum (ESI) 540 (M+1).

Workup

  1. customwas evacuated
  2. custompurged three times with Ar
  3. additionPd(Ph3P)4 (23 mg) was added
  4. customthe mixture was evacuated
  5. custompurged again with Ar
  6. temperatureThe mixture was heated
  7. temperatureto reflux
  8. filtrationfiltered through Celite
  9. concentrationconcentrated
  10. customThe residue was purified by preparative thin-layer chromatography
  11. washeluting with 95:5 CH2Cl2-2M NH3 in MeOH

Sources & evidence

ORD record
ord-56273d3c03404e39ab06bbe436741f17
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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