4-Toluenesulfonyl chloride → 8-Bromoisoquinolin-6-yl 4-methylbenzenesulfonate

HRID 2069084Notes

Reaction equation

HRID 2069084 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([OH:19])[CH:12]=[C:13]2[C:18]=1[CH:17]=[N:16][CH:15]=[CH:14]2.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:19][C:11]2[CH:12]=[C:13]3[C:18](=[C:9]([Br:8])[CH:10]=2)[CH:17]=[N:16][CH:15]=[CH:14]3)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1357421998-Bromoisoquinolin-6-ol

Product 1

HCID 866464828-Bromoisoquinolin-6-yl 4-methylbenzenesulfonateYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.137 mL) was added to a dichloromethane (5 mL) solution of Intermediate 7 (100 mg) and p-toluenesulfonic acid chloride (66 mg; WAKO) at room temperature and the resulting mixture was stirred as it was for 15 hours. The resulting mixture was diluted with dichloromethane and washed with water, the organic layer was dried, then the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate) to give the title compound (92.9 mg).

Workup

  1. washwashed with water
  2. customthe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d6f0b27ceff3465a83abc69287845141
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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