Triethylamine → HCID 136359796, compound

HRID 2361385Notes

Reaction equation

HRID 2361385 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[C:16]=4[CH3:24])=[N:13][NH:12][C:11](=[O:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1.C([Sn](CCCC)(CCCC)[C:31]([O:33]CC)=[CH2:32])CCC.C(N(CC)CC)C>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:31]([C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[C:16]=4[CH3:24])=[N:13][NH:12][C:11](=[O:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1)(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 136359795HCID 136359795, compound

Product 1

HCID 136359796HCID 136359796, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 7-bromo-1-(2-methyl-3-nitrophenyl)-3H-pyridazino [4,5-b]indol-4(5H)-one (2.00 g, 5.01 mmol), tributyl(1-ethoxyvinyl)stannane (4.06 mL, 12.02 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.422 g, 0.601 mmol), and triethylamine (0.908 mL, 6.51 mmol) in 1,4-Dioxane (100 mL) was heated at 95° C. for 24 hr. Upon cooling to room temperature, the mixture was filtered through CELITE®. The filtrate was concentrated under vacuum to dryness. To the residue was added THF (100 mL) and 1 N HCl solution (100 mL), and the mixture was stirred at 60° C. for 1.5 hr. It was concentrated under vacuum to a volume of 100 mL, neutralized with 1 N NaOH solution to pH 4-5, and extracted with ethyl acetate (3×150 mL). The combined, cloudy organic solution was concentrated under vacuum to dryness. To the residue was added hexane (100 mL), and the mixture was stirred at room temperature for 1 hr. The clear solution was decanted and the residue was repeated with this operation for two more times. The solid material was collected by suction filtration to give a crude product (1.98 g, 5.46 mmol, >100% yield) as a beige solid.

Workup

  1. temperatureUpon cooling to room temperature
  2. filtrationthe mixture was filtered through CELITE®
  3. concentrationThe filtrate was concentrated under vacuum to dryness
  4. additionTo the residue was added THF (100 mL) and 1 N HCl solution (100 mL)
  5. concentrationIt was concentrated under vacuum to a volume of 100 mL
  6. extractionextracted with ethyl acetate (3×150 mL)
  7. concentrationcloudy organic solution was concentrated under vacuum to dryness
  8. additionTo the residue was added hexane (100 mL)
  9. stirringthe mixture was stirred at room temperature for 1 hr
  10. customThe clear solution was decanted
  11. filtrationThe solid material was collected by suction filtration

Sources & evidence

ORD record
ord-a6aa1c45dbca4d14835e202c4948085e
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…