HCID 20063329, compound → HCID 20063370, compound

HRID 1084450Notes

Reaction equation

HRID 1084450 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2/[CH:22]=[CH:23]/[C:24](Cl)=[O:25])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([CH:19]([CH3:20])[CH3:21])[C:9]=2/[CH:22]=[CH:23]/[CH:24]=[O:25])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 20063329HCID 20063329, compound

Product 1

HCID 20063370HCID 20063370, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The (E)-3-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]prop-2-enoyl chloride, prepared as described in section (i), was dissolved in dry toluene (10 ml). The solution was flushed with nitrogen, and then it was treated with tetrakis(triphenylphosphine)palladium(0) (58 mg). The mixture was then treated with tributyltin hydride (0.27 ml), dropwise, during 5 minutes and the resulting mixture was stirred at room temperature for 90 minutes. The solvent was then evaporated off and the residue was subjected to flash chromatography on silica gel, using ethyl acetate as eluent. The product was triturated with petroleum ether (b.p. 60°-80° C.), to give (E)-3-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]prop-2-enal (100 mg) in the form of a yellow solid, m.p. 159°-161° C. [Elemental analysis: C, 75.0; H, 5.44; N, 4.13; F, 5.86%; calculated: C, 75.21; H, 5.41; N, 4.18; F, 5.67%].

Workup

  1. customThe solution was flushed with nitrogen
  2. additionit was treated with tetrakis(triphenylphosphine)palladium(0) (58 mg)
  3. additionThe mixture was then treated with tributyltin hydride (0.27 ml)
  4. customThe solvent was then evaporated off
  5. customThe product was triturated with petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-fb75445fa03f45b7ba610f63818c0968
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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