Allyl Alcohol → HCID 86616094, compound

HRID 1783761Notes

Reaction equation

HRID 1783761 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N+:4]([O-:12])[CH:3]=1.[Cl-].[Li+].C(N(CC)CC)C.[CH2:22]([OH:25])[CH:23]=[CH2:24]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O-:12][N+:4]1[CH:3]=[C:2]([CH2:24][CH2:23][CH:22]=[O:25])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 433294Lithium ChlorideHCID 8173234-Bromoisoquinoline N-oxide

Product 1

HCID 86616094HCID 86616094, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-bromoisoquinoline 2-oxide (5-2) (500 mg, 2.23 mmol, 1.0 equiv), lithium chloride (95 mg, 2.23 mmol, 1.0 equiv) and palladium(II) acetate (20.04 mg, 0.089 mmol, 0.04 equiv) were dissolved in anhydrous DMF (8.6 mL). To this orange solution, was added triethylamine (933 μl, 6.69 mmol, 3.0 equiv) and allyl alcohol (308 μl, 4.46 mmol, 2.0 equiv). The reaction mixture was heated at 100° C. for 1.5 hours. Black precipitate was formed. And LCMS showed the starting material was completely consumed. The reaction mixture was filtered, and washed with EtOAc, then concentrated. The crude was purified with silica gel chromatography (MeOH/EtOAc=0->20%) to afford the compound (5-3). LRMS m/z (M+H) 202.1 found, 202.2 required.

Workup

  1. customBlack precipitate was formed
  2. customwas completely consumed
  3. filtrationThe reaction mixture was filtered
  4. washwashed with EtOAc
  5. concentrationconcentrated
  6. customThe crude was purified with silica gel chromatography (MeOH/EtOAc=0->20%)

Sources & evidence

ORD record
ord-fa85eaad65b04089ba25b7f5b3de3c66
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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