Triethylamine → Perfluorophenyl 1-chloroisoquinoline-6-sulfonate

HRID 1473329Notes

Reaction equation

HRID 1473329 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[OH:12].[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([S:24](Cl)(=[O:26])=[O:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([S:24]([O:12][C:3]3[C:2]([F:1])=[C:7]([F:8])[C:6]([F:9])=[C:5]([F:10])[C:4]=3[F:11])(=[O:26])=[O:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 861938101-Chloroisoquinoline-6-sulfonyl chloride

Product 1

HCID 86687382Perfluorophenyl 1-chloroisoquinoline-6-sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3,4,5,6-Pentafluorophenol (2.73 g, 14.82 mmol) was dissolved in DCM (49.4 ml). 1-chloroisoquinoline-6-sulfonyl chloride (2.59 g, 9.88 mmol) was added, followed by the dropwise addition of triethylamine (2.066 ml, 14.82 mmol). The reaction was stirred overnight at room temperature. The reaction was concentrated and purified by silica gel chromatography (40 g column, gradient elution 0 to 50% Et2O:Heptane) to afford perfluorophenyl 1-chloroisoquinoline-6-sulfonate as a white solid. m/z (ESI) 410.0 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography (40 g column, gradient elution 0 to 50% Et2O:Heptane)

Sources & evidence

ORD record
ord-769f01ae538b4f2fbf9cc92960830916
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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