Allyl Alcohol → 6-Quinoxalinepropanal

HRID 1257846Notes

Reaction equation

HRID 1257846 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2.[CH2:12]([OH:15])[CH:13]=[CH2:14].C1(N(C)C2CCCCC2)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH2:14][CH2:13][CH:12]=[O:15])=[CH:11][CH:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 7858Allyl AlcoholHCID 24210N-Methyl dicyclohexylamineHCID 6109396-Bromoquinoxaline

Product 1

HCID 866215076-QuinoxalinepropanalYield 55.1%

Reagents, catalysts & solvents 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 6-bromoquinoxaline (0.40 g, 1.9 mmol), 2-propen-1-ol (0.260 mL, 3.8 mmol), tris(dibenzylideneacetone)dipalladium (26 mg, 0.029 mmol), tri-tert-butylphosphonium tetrafluoroborate (16 mg, 0.057 mmol) and N-cyclohexyl-N-methyl-cyclohexanamine (0.49 mL, 2.3 mmol) in 1,4-dioxane (3.0 mL) was stirred at 40° C. overnight. After cooling to RT, the mixture was filtered, washed with methylene chloride and the filtrate was concentrated. The crude material was purified by chromatography on silica gel with EtOAc in Hexane (0-40%) to afford the desired product (195 mg). LCMS: (M+H)=187.3.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe mixture was filtered
  3. washwashed with methylene chloride
  4. concentrationthe filtrate was concentrated
  5. customThe crude material was purified by chromatography on silica gel with EtOAc in Hexane (0-40%)

Sources & evidence

ORD record
ord-1d2b7df4eecd4cb0a7afc385e9546b25
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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