Sodium Bicarbonate → HCID 68469403, compound

HRID 387679Notes

Reaction equation

HRID 387679 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1.[C:24](=O)(O)[O-].[Na+]>O1CCOCC1.O.CN(C)C=O>[CH3:24][C:2]1[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]2[CH2:6][CH2:7][N:8]([CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[C:9](=[O:12])[C:10]=2[CH:11]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 68473018HCID 68473018, compound

Product 1

HCID 68469403HCID 68469403, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Added to a solution of 0.385 g of methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate in 9.6 cm3 of dioxane, 2 cm3 of water and one drop of dimethylformamide, at a temperature close to 20° C., are 190 mg of sodium bicarbonate. The reaction medium is then degassed under an argon atmosphere, then 58 mg of methylboronic acid and 93 mg of tetrakis(triphenylphosphine)palladium are added. The mixture is heated at 150° C. in a microwave oven for 8 minutes, cooled to a temperature close to 20° C., filtered and concentrated to dryness under reduced pressure (5 kPa). The filtrate is taken up by 20 cm3 of dichloromethane and 10 cm3 of water. The organic phase is extracted, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa). The residual solution (around 4 cm3) is purified by flash chromatography over silica (column: 50 g; spherical silica of BP-SUP type, particle size: 20-40 μm; eluent: 80% heptane/20% ethyl acetate then 60% heptane/40% ethyl acetate then 100% ethyl acetate). After concentrating the fractions under reduced pressure, 35 mg of methyl 7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are obtained in the form of a colorless oil.

Workup

  1. customclose to 20° C.
  2. customThe reaction medium is then degassed under an argon atmosphere
  3. addition58 mg of methylboronic acid and 93 mg of tetrakis(triphenylphosphine)palladium are added
  4. temperaturecooled to a temperature
  5. customclose to 20° C.
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (5 kPa)
  8. extractionThe organic phase is extracted
  9. washwashed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure (5 kPa)
  13. customThe residual solution (around 4 cm3) is purified by flash chromatography over silica (column
  14. concentrationAfter concentrating the fractions under reduced pressure, 35 mg of methyl 7-methyl-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate
  15. customare obtained in the form of a colorless oil

Sources & evidence

ORD record
ord-4a2dca2aecc34a83ae38b28b5c9e1972
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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