Potassium Carbonate → (4-Fluoro-benzyl)-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-amine

HRID 8645

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:47]=[CH:46][C:43]([CH2:44][NH2:45])=[CH:42][CH:41]=1.C(=O)([O-])[O-].[K+].[K+]>>[F:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][NH:45][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[C:16]4[S:17][CH:18]=[CH:19][C:15]=4[O:14][N:13]=3)[CH:7]=2)=[CH:42][CH:41]=1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 673264-Fluorobenzylamine

HCID 219835563-[3-(3-Chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole

HCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 21983558(4-Fluoro-benzyl)-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl]-amineYield 94%

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, 4-fluorobenzylamine and potassium carbonate essentially as described above in example 4. Combine the appropriate fractions and concentrate to give the title compound (0.36 g, 94% Yield) as an oil. Purity by LC/MS (APCI)=100% area, [M+H]+=383 m/e.

Workup

concentrationCombine the appropriate fractions and concentrate

Sources & evidence

ORD record: ord-598260d8b1be4001a4fe9d3ea45a3d59
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091199B1

Linked notes

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