Sodium Bicarbonate → HCID 68473665, compound

HRID 387675Notes

Reaction equation

HRID 387675 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(=O)(O)[O-].[Na+]>O1CCOCC1.O>[C:9]([C:10]1[CH:11]=[CH:2][CH:3]=[CH:4][C:5]=1[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)#[N:8]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 68473018HCID 68473018, compound

Product 1

HCID 68473665HCID 68473665, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Added to a solution of 0.4 g of methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate in 12.5 cm3 of dioxane and 2.5 cm3 of water, at a temperature close to 20° C., are 196 mg of sodium bicarbonate. The reaction medium is then degassed under an argon atmosphere, then 147.5 mg of 2-cyanophenylboronic acid and 96 mg of tetrakis(triphenylphosphine)palladium are added. The mixture is heated at 150° C. in a microwave oven for 4 minutes, cooled to a temperature close to 20° C. and filtered. The filtrate is taken up by 20 cm3 of dichloromethane and 20 cm3 of water. The organic phase is extracted, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa). The residual solution (around 3 cm3) is purified by flash chromatography over silica (column: 50 g; spherical silica of BP-SUP type, partical size: 20-40 μm; eluent: 80% heptane/20% ethyl acetate then 60% heptane/40% ethyl acetate then 50% heptane/50% ethyl acetate). After concentrating the fractions under reduced pressure, 178 mg of methyl 7-(2-cyanophenyl)-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. addition147.5 mg of 2-cyanophenylboronic acid and 96 mg of tetrakis(triphenylphosphine)palladium are added
  4. temperaturecooled to a temperature
  5. customclose to 20° C.
  6. filtrationfiltered
  7. extractionThe organic phase is extracted
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure (5 kPa)
  11. customThe residual solution (around 3 cm3) is purified by flash chromatography over silica (column
  12. concentrationAfter concentrating the fractions under reduced pressure, 178 mg of methyl 7-(2-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate
  13. customare obtained in the form of a colorless oil

Sources & evidence

ORD record
ord-a557dfc091dd4c05874c3d6ef605f29f
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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