Hydrochloric Acid → HCID 23160764, compound

HRID 1867229Notes

Reaction equation

HRID 1867229 reaction equation
C([Sn](CCCC)(CCCC)[C:6]([O:8]CC)=[CH2:7])CCC.Br[C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH2:22][C:23]([CH3:41])([CH3:40])[N:24]=[C:25]2[C:30]1[CH:31]=[N:32][C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2.Cl.O.[NH4+]>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.C1(C)C=CC=CC=1>[C:6]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH2:22][C:23]([CH3:41])([CH3:40])[N:24]=[C:25]2[C:30]1[CH:31]=[N:32][C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 22024077Azanium;hydrateHCID 23160933HCID 23160933, compound

Product 1

HCID 23160764HCID 23160764, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Tributyl (1-ethoxyvinyl) tin (0.85 mL, 2.4 mmol) and dichlorobis(triphenylphosphine)palladium (15.8 mg, 0.022 mmol) were added to a toluene solution (0.9 mL) of 3-(5-bromo-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (806 mg, 2.2 mmol), and after stirring for 3 hours at 100° C., dilute hydrochloric acid was added to temporarily acidify followed by basifying with ammonium water, filtering, concentrating the filtrate and applying the resulting residue to chromatography to obtain 647 mg of the target compound (yield: 89%).

Workup

  1. filtrationfiltering
  2. concentrationconcentrating the filtrate

Sources & evidence

ORD record
ord-91834abc044d478b9152eabb98e1c9ae
Source dataset
uspto-grants-2009_12
Patent number
US07632783B2

Reaction notes

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