Azetidine → 6-(4-Azetidin-1-yl-but-1-ynyl)-3-(4-bromo-phenyl)-benzo[d]isothiazole

HRID 347110Notes

Reaction equation

HRID 347110 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH2:19][CH2:20]OS(C)(=O)=O)=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[NH:26]1[CH2:29][CH2:28][CH2:27]1>CC(N(C)C)=O.CCOCC.C([O-])([O-])=O.[Na+].[Na+]>[N:26]1([CH2:20][CH2:19][C:18]#[C:17][C:15]2[CH:14]=[CH:13][C:12]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)=[N:9][S:10][C:11]=3[CH:16]=2)[CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 2

HCID 10422AzetidineHCID 57428078HCID 57428078, compound

Product 1

HCID 223140526-(4-Azetidin-1-yl-but-1-ynyl)-3-(4-bromo-phenyl)-benzo[d]isothiazoleYield 34.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 10340Sodium CarbonateSolventHCID 31374DimethylacetamideSolvent

Procedure

73 mg (0.16 mmol) Methanesulfonic acid 4-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-ynyl ester in 1 ml DMA were treated with 35 μl (0.5 mmol) azetidine for 48 h. The solution was diluted with ether and aqueous Na2CO3, the phases were separated and the inorganic layer was extracted with ether. The combined organic phases were washed with brine, dried over Na2SO4. Column chromatography on silica gel with a gradient CH2Cl2 to CH2Cl2:MeOH 8:1 gave 22.2 mg (33%) 6-(4-Azetidin-1-yl-but-1-ynyl)-3-(4-bromo-phenyl)-benzo[d]isothiazole as brown oil, MS: 397 (MH+, 1Br).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic layer was extracted with ether
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-f877151368bd4d3cb3d4231f8276ffbe
Source dataset
uspto-grants-2007_02
Patent number
US07173043B2

Reaction notes

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