Water → HCID 68644565, compound

HRID 1159004Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C@@:18]1([CH2:22][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[C@H:20]([CH3:21])[O:19]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C@:18]([OH:19])([C@H:20]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1)[CH3:21])[CH2:22][N:23]1[CH:27]=[N:26][CH:25]=[N:24]1

Participants

Conditions

Temperature: 180 °C

Procedure

To a suspension of indazole (0.059 g, 0.5 mmol), 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole (0.105 g, 0.416 mmol) in N,N′-dimethylformamide (2.5 ml) was added anhydrous potassium carbonate (0.069 g, 0.5 mmol), followed by radiating microwaves thereon with stirring at 180° C. for 5 min. Thereafter, the addition of water (0.5 ml) at 0° C. terminated the reaction. The reaction solution was diluted with ethyl acetate (10 ml) and washed with saturated ammonium chloride solution (10 ml) and then with brine (10 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated in a vacuum. The crude product was purified by chromatography on silica gel to give the title compound (Yield 44%).

Workup

customterminated
customthe reaction
washwashed with saturated ammonium chloride solution (10 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated in a vacuum
customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-2eb812d34445441891e26391a629067f
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812045B2

Reaction notes

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