Cesium carbonate → 3-((3-Methyloxetan-3-yl)methoxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole

HRID 1482869Notes

Reaction equation

HRID 1482869 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][N:16]=[C:15]([OH:18])[C:14]=3[CH:19]=2)=[CH:6][CH:5]=1.Br[CH2:23][C:24]1([CH3:28])[CH2:27][O:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].O1C2C=CC=CC=2C=N1>CN(C=O)C.C(OCC)(=O)C>[CH3:23][C:24]1([CH2:28][O:18][C:15]2[C:14]3[CH:19]=[C:10]([C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:5][CH:6]=4)[CH:11]=[CH:12][C:13]=3[O:17][N:16]=2)[CH2:27][O:26][CH2:25]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 710731,2-BenzisoxazoleHCID 144860Oxetane, 3-(bromomethyl)-3-methyl-HCID 178518982HCID 178518982, compound

Product 1

HCID 1181619323-((3-Methyloxetan-3-yl)methoxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazoleYield 61.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-ol (100 mg, 0.34 mmol), 3-bromomethyl-3-methyloxetane (150 mg, 0.91 mmol) and cesium carbonate (300 mg) were combined in 5 mL DMF and stirred at ambient temperature until HPLC showed complete disappearance of benzisoxazole starting material. The reaction mixture was diluted with 60 mL ethyl acetate, washed with water and brine and evaporated under vacuum. Flash chromatographic purification on 12 g silica gel with 0-60% ethyl acetate in hexane gave the title compound (80 mg, 0.21 mmol).

Workup

  1. washwashed with water and brine
  2. customevaporated under vacuum
  3. customFlash chromatographic purification on 12 g silica gel with 0-60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d95816126c8f44769fde3c0ae3d6ab27
Source dataset
uspto-grants-2016_08
Patent number
US09416115B2

Reaction notes

Loading…