Trifluoromethanesulfonic acid → 5-Iodoisoquinoline-6-ol

HRID 1022856Notes

Reaction equation

HRID 1022856 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[B-](F)(F)(F)F.C1C=CN=CC=1.C1C=CN=CC=1.[IH2+:29].FC(F)(F)S(O)(=O)=O>ClCCl>[I:29][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 135483582Isoquinolin-6-ol

Product 1

HCID 1360928975-Iodoisoquinoline-6-olYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under argon atmosphere 1.77 g (12.2 mmol) of compound 7 were added to a solution of 5.0 g (13.5 mmol) bis(pyridin)iodonium tetrafluoroborate in 100 mL of dry dichloromethane. A solution of 2.4 mL (4 g, 26.8 mmol) trifluoromethane sulfonic acid in 20 mL dry dichloromethane was added dropwise at 0° C. and the mixture was stirred for 3 hours at room temperature. The solvents were removed by distillation and the remainder was treated with aqueous NaHCO3 solution. The precipitate was filtered, washed with water and dried to yield 3.2 g (97%) of compound 10 as a beige solid.

Workup

  1. customThe solvents were removed by distillation
  2. additionthe remainder was treated with aqueous NaHCO3 solution
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c53df842b66c465ba2aaf0292e97a46d
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

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