1,4-Dioxane → HCID 71245573, compound

HRID 1845913Notes

Reaction equation

HRID 1845913 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.O1CCOCC1.CCN(C(C)C)C(C)C>CO.C([O-])(=O)C.C([O-])(=O)C.[Cu+2]>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:13]([F:24])([F:23])[F:12])[CH:19]=3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 1884446-Bromo-2,3-dihydro-1,3-benzothiazol-2-oneHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 71245573HCID 71245573, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent

Procedure

To a round bottom flask was added 6-bromo-1,3-benzothiazol-2(3H)-one (0.050 g, 0.217 mmol), copper(2+) diacetate (0.079 g, 0.435 mmol), [3-(trifluoromethyl)phenyl]boronic acid (0.124 g, 0.652 mmol), Dioxane (1 mL), and DIPEA (0.114 mL, 0.652 mmol). The reaction mixture was then permitted to stir open to the atmosphere for ˜17 hours (overnight). The crude reaction mixture was then diluted with methanol, filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 30% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) gave 6-bromo-3-[3-(trifluoromethyl)phenyl]-1,3-benzothiazol-2(3H)-one (15-1) as a white solid. HRMS (M+H)+: observed=373.9455, calculated=373.9457.

Workup

  1. customThe crude reaction mixture
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification of crude
  5. customreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 30% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water)

Sources & evidence

ORD record
ord-ff28e667f66b4ef7a7001506bf344bf1
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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