Water → 3-(Oxetan-2-ylmethoxy)-5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazole

HRID 1482866Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]3N=CC=CN=3)[C:6]=2[CH:18]=1.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.[C:33](=[O:36])([O-])[O-].[K+].[K+].O.[CH3:40]N(C=O)C>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:36]1[CH2:33][CH2:40][CH:12]1[CH2:11][O:10][C:7]1[C:6]2[CH:18]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([O:21][C:20]([F:32])([F:31])[F:19])=[CH:23][CH:24]=3)[CH:3]=[CH:4][C:5]=2[O:9][N:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-Bromo-3-(pyrimidin-2-ylmethoxy)benzo[d]isoxazole (114 mg, 0.40 mmol), 4-(trifluoromethoxy)phenylboronic acid (100 mg, 0.49 mmol), potassium carbonate (500 mg), and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (25 mg, 0.034 mmol) were combined in 3 mL DMF. 1.5 mL water was added and the mixture was stirred at 60° C. for 30 minutes. 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 (115 mg, 0.31 mmol).

Workup

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

Sources & evidence

ORD record: ord-b9760a04e7f54eab9dbf7f444b895807
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416115B2

Reaction notes

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