Potassium Carbonate → [2-(3-Thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-(2-trifluoromethylbenzyl)-amine

HRID 8667

Reaction equation

HRID 8667 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]([F:36])([F:35])[C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>C(#N)C>[O:13]1[C:14]2[CH:18]=[CH:17][S:16][C:15]=2[C:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[O:4][CH2:3][CH2:2][NH:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[C:26]([F:25])([F:35])[F:36])=[N:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 764472-(Trifluoromethyl)benzylamineHCID 219835823-[3-(2-Bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 21983566[2-(3-Thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-(2-trifluoromethylbenzyl)-amineYield 96.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.250 g, 0.771 mmol), potassium carbonate (0.205 g, 1.48 mmol), 2-(trifluoromethyl)benzylamine (0.676 mg, 3.86 mmol) and acetonitrile (4 mL) essentially as described above in example 18 except that the reaction is run overnight and the compound is purified by column using a solvent gradient of 5% ethyl acetate in dichloromethane to 10% methanol in ethyl acetate to give the title compound (0.311 g, 96% Yield). Purity by LC/MS (APCI)=99%, [M+H]+=419.

Workup

  1. customthe compound is purified by column

Sources & evidence

ORD record
ord-7425231cb5054edb8397a2b558164d3f
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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