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

HRID 270339
Notes
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Reaction equation

HRID 270339 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 CarbonateSolvent
HCID 31374
Dimethylacetamide
Solvent

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-2ee84c923ef746bcae1f1208f24a3392
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07449483B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes