Trifluoroacetic acid → HCID 59375136, compound

HRID 661835Notes

Reaction equation

HRID 661835 reaction equation
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH:17](O)[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66606820HCID 66606820, compound

Product 1

HCID 59375136HCID 59375136, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 A solution of crude 2-(3-bromo-2-methylphenyl)-3-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (600 mg, 1.806 mmol) in DCM (30 mL) was treated with triethylsilane (15 mL, 94 mmol) and the resulting mixture was treated slowly with TFA (1.392 mL, 18.06 mmol). The mixture was stirred at rt for 2 h, then was concentrated and the residue was dissolved in DCM. The solution was washed with NaHCO3 (aq) and water, then was dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 to 60:40 hexane-EtOAc) to give 2-(3-bromo-2-methylphenyl)isoquinolin-1(2H)-one as a white solid (380 mg, 67%). Mass spectrum m/z 314, 316 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in DCM
  3. washThe solution was washed with NaHCO3 (aq) and water
  4. customwas dried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (
  7. washeluting with a gradient from 80:20 to 60:40 hexane-EtOAc)

Sources & evidence

ORD record
ord-5a734ef6e4cb4be7881929fc1d306468
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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