Potassium Carbonate → HCID 58574162, compound

HRID 1619408Notes

Reaction equation

HRID 1619408 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[N:7]3[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.Br[C:20]1C=[C:28]2[C:23]([C:24](=[O:36])[N:25]3[CH2:33][C:32]([CH3:35])([CH3:34])[CH2:31][CH2:30][C:26]3=[N:27]2)=[CH:22][CH:21]=1.C[C:38]1([CH3:47])[C:42]([CH3:44])([CH3:43])OB(C=C)O1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:16][C:13]1([CH3:17])[CH2:14][CH2:15][N:7]2[C:8](=[N:9][C:10]3[C:5]([C:6]2=[O:18])=[CH:4][CH:3]=[C:2]([CH:20]=[CH2:21])[CH:11]=3)[CH2:12]1.[CH3:34][C:32]1([CH3:35])[CH2:33][N:25]2[C:26](=[N:27][C:28]3[C:23]([C:24]2=[O:36])=[CH:22][CH:43]=[C:42]([CH:38]=[CH2:47])[CH:44]=3)[CH2:30][CH2:31]1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 58574181HCID 58574181, compoundHCID 58574356HCID 58574356, compound

Product 2

HCID 58574162HCID 58574162, compoundHCID 58574574HCID 58574574, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-bromo-7,7-dimethyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one, 3-bromo-8,8-dimethyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one (2.0 g, 6.4 mmol, 1 equiv), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (2.2 g, 12.8 mmol, 2 eq), K2CO3 (1.76 g, 12.8 mmol, 2 equiv), Pd(OAc)2 (576 mg, 2.56 mmol, 0.4 equiv) and Ph3P (1.34 g, 5.12 mmol, 0.8 equiv) in dioxane (200 mL) was stirred at 85° C. for 4 hours under N2. After that, the reaction mixture was cooled to rt. The reaction was quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extract was dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography to afford 650 mg of 7,7-dimethyl-3-vinyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one and 1.0 g of 8,8-dimethyl-3-vinyl-8,9-dihydro-6H-pyrido[2,1-b]quinazolin-11(7H)-one. MS (ESI): 255 (MH+).

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cd502a8d3b7842aeb05e1bf20e78d9c2
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…