Cesium carbonate → HCID 67467679, compound

HRID 1845905Notes

Reaction equation

HRID 1845905 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.CN1C(=O)CCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH:27]1[CH2:29][C:28]1([F:31])[F:30]>C(OCC)(=O)C.O.O1CCOCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH2:26][CH:27]3[CH2:29][C:28]3([F:31])[F:30])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 1884446-Bromo-2,3-dihydro-1,3-benzothiazol-2-oneHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropane

Product 1

HCID 67467679HCID 67467679, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a round bottom flask was added 6-bromo-1,3-benzothiazol-2(3H)-one (11.1 g, 48.5 mmol), anhydrous NMP (10 mL), anhydrous 1,4-dioxane (100 mL), cesium carbonate (33.2 g, 102 mmol), followed by 2-(bromomethyl)-1,1-difluorocyclopropane (8.29 g, 48.5 mmol). The reaction mixture was then heated to 95° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 18 hours. The crude reaction mixture was then cooled to room temperature, suspended in ethyl acetate and washed with a saturated solution of sodium bicarbonate, followed by water, then brine, dried over sodium sulfate, filtered, and concentrated. The resulting residue was then purified by silica gel chromatography (0-30% EtOAc/Hex) to give 6-bromo-3-[(2,2-difluorocyclopropyl)methyl]-1,3-benzothiazol-2(3H)-one (1-1) as a white solid. HRMS (M+H)+: observed=319.9550, calculated=319.9551.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customThe crude reaction mixture
  4. temperaturewas then cooled to room temperature
  5. washwashed with a saturated solution of sodium bicarbonate
  6. dry with materialbrine, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was then purified by silica gel chromatography (0-30% EtOAc/Hex)

Sources & evidence

ORD record
ord-a4f519fcd6ed4b489e73a2d3d5fb0aa3
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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