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Potassium Carbonate → 3-(3-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propoxy}-phenyl)-thieno[2,3-d]isoxazole

HRID 8653
Notes
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Reaction equation

HRID 8653 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.ClCCCOC1C=C(C2C3SC=CC=3ON=2)C=CC=1.[F:39][C:40]1[CH:45]=[CH:44][C:43]([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)=[CH:42][CH:41]=1.C(=O)([O-])[O-].[K+].[K+]>>[F:39][C:40]1[CH:41]=[CH:42][C:43]([N:46]2[CH2:51][CH2:50][N:49]([CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:7]=[C:8]([C:12]4[C:16]5[S:17][CH:18]=[CH:19][C:15]=5[O:14][N:13]=4)[CH:9]=[CH:10][CH:11]=3)[CH2:48][CH2:47]2)=[CH:44][CH:45]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 752601-(4-Fluorophenyl)piperazineHCID 219835563-[3-(3-Chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazoleHCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 219835533-(3-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propoxy}-phenyl)-thieno[2,3-d]isoxazoleYield 100%

Procedure

The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 1-(4-fluorophenyl) piperazine and potassium carbonate essentially as described above in example 4 except that the column is eluted with a mixture of dichloromethane:methanol (99:1). Combine the appropriate fractions and concentrate to give the title compound (0.44 g, 100% Yield) as a solid. Purity by LC/MS (APCI)=100% area, [M+H]+=438 m/e.

Workup

  1. washis eluted with a mixture of dichloromethane:methanol (99:1)
  2. concentrationCombine the appropriate fractions and concentrate

Sources & evidence

ORD record
ord-f34ce8945daf4fefa0c5f1821d2e0803
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091199B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes