Triethylamine → HCID 86687467, compound

HRID 1473418Notes

Reaction equation

HRID 1473418 reaction equation
C(SC1C=C2C(C(Br)=CN=C2)=CC=1)C1C=CC=CC=1.[Br:20][C:21]1[C:30]2[C:25](=[CH:26][C:27]([S:31](Cl)(=[O:33])=[O:32])=[CH:28][CH:29]=2)[CH:24]=[N:23][CH:22]=1.[F:35][C:36]1[C:41]([F:42])=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:37]=1[OH:46].C(N(CC)CC)C>O.C(O)(=O)C.C(#N)C>[Br:20][C:21]1[C:30]2[C:25](=[CH:26][C:27]([S:31]([O:46][C:37]3[C:36]([F:35])=[C:41]([F:42])[C:40]([F:43])=[C:39]([F:44])[C:38]=3[F:45])(=[O:33])=[O:32])=[CH:28][CH:29]=2)[CH:24]=[N:23][CH:22]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 86687466HCID 86687466, compoundHCID 86687468HCID 86687468, compound

Product 1

HCID 86687467HCID 86687467, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a vial charged with 7-(benzylthio)-4-bromoisoquinoline (0.570 g, 1.726 mmol) was added acetonitrile (16.24 ml), acetic acid (0.609 ml), water (0.406 ml). The resulting solution was cooled in an ice water bath and 1,3-dichloro-5,5-dimethyl-2-imidazolidinedione (0.453 ml, 3.45 mmol) was added. After 1 hr LC/MS of the resulting solution indicated product, 4-bromoisoquinoline-7-sulfonyl chloride, as the primary species. m/z (ESI) 306.0 (M+H)+. To the mixture was added 2,3,4,5,6-pentafluorophenol (0.361 ml, 3.45 mmol) and triethylamine (0.962 ml, 6.90 mmol) affording a yellow solution. After 45 min LC/MS indicated conversion to desired product (PFP ester). The mixture was diluted with EtOAc and extracted with H2O. The aqueous phase was extracted with EtOAc. The combined organics were dried with Na2SO4, filtered, and dried under reduced pressure. The crude material was purified with a 40 g silicycle HP column (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0-15%) providing product as a pale yellow oil, perfluorophenyl 4-bromoisoquinoline-7-sulfonate (0.618 g, 1.361 mmol, 79% yield). m/z (ESI) 454.1 (M+H)+.

Workup

  1. temperatureThe resulting solution was cooled in an ice water bath
  2. customaffording a yellow solution
  3. waitAfter 45 min LC/MS indicated

Sources & evidence

ORD record
ord-c96bee10fd014c93960cfc1feba7e91c
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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