Sodium Bicarbonate → HCID 68473716, compound

HRID 387672Notes

Reaction equation

HRID 387672 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:5]=[C:4]([C:2]2[CH:3]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:5]3[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]=3[CH:11]=2)[CH:3]=[CH:2][CH:11]=1)#[N:8]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 68473018HCID 68473018, compound

Product 1

HCID 68473716HCID 68473716, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Added to a solution of 0.3 g of methyl 7-bromo-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate in 9.4 cm3 of dioxane and 1.8 cm3 of water, at a temperature close to 20° C., are 147 mg of sodium bicarbonate. The reaction medium is then degassed under an argon atmosphere, then 111 mg of 3-cyanophenylboronic acid and 72 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 dried over anhydrous magnesium sulfate then filtered; added to the filtrate is 1 g of silica and the absorbed residue is purified by flash chromatography over silica (column: 15 g; spherical silica of BP-SUP type, particle size: 20-40 μm, eluent: 80% heptane/20% ethyl acetate then 60% heptane/40% ethyl acetate). After concentrating the fractions under reduced pressure, 103 mg of methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are obtained in the form of an orange oil.

Workup

  1. customclose to 20° C.
  2. customThe reaction medium is then degassed under an argon atmosphere
  3. addition111 mg of 3-cyanophenylboronic acid and 72 mg of tetrakis(triphenylphosphine)palladium are added
  4. temperaturecooled to a temperature
  5. customclose to 20° C.
  6. filtrationfiltered
  7. dry with materialThe filtrate is dried over anhydrous magnesium sulfate
  8. filtrationthen filtered
  9. additionadded to the filtrate
  10. customthe absorbed residue is purified by flash chromatography over silica (column
  11. concentrationAfter concentrating the fractions under reduced pressure, 103 mg of methyl 7-(3-cyanophenyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate
  12. customare obtained in the form of an orange oil

Sources & evidence

ORD record
ord-f1a425bffd274329a8061377846cb5f2
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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