Sodium hydride → HCID 17966051, compound

HRID 1602053Notes

Reaction equation

[CH3:1][N:2]1[C:6]([O:7][C:8]2[C:13]([F:14])=[C:12]([CH3:15])[C:11]([F:16])=[C:10](F)[N:9]=2)=[CH:5][C:4]([C:18]([F:21])([F:20])[F:19])=[N:3]1.[H-].[Na+].[F:24][C:25]1[CH:26]=[C:27]([OH:32])[CH:28]=[CH:29][C:30]=1[F:31]>S1(CCCC1)(=O)=O.CCCCC.C(OCC)(=O)C>[F:14][C:13]1[C:8]([O:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:5]=2)=[N:9][C:10]([O:32][C:27]2[CH:28]=[CH:29][C:30]([F:31])=[C:25]([F:24])[CH:26]=2)=[C:11]([F:16])[C:12]=1[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-3,5,6-trifluoropyridine (1.2 g, 4 mmol; see Example 2), 60% sodium hydride (0.2 g, 4 mmol) and 3,4-difluorophenol (0.65 g, 5 mmol) in anhydrous sulfolane (5 ml) is heated to 90° C. overnight. The reaction mixture is diluted with pentane/ethyl acetate (1/1 by volume) and filtered through a bed of silica gel. The filtrate is washed 8 times with water, the organic layer is dried with anhydrous magnesium sulfate, and the solvents are removed in vacuo. The residue is purified by a flash silica gel chromatography using pentane/ethyl acetate in a ratio of 9/1. 0.9 g (53% yield) of the title compound are obtained as a colourless solid, m.p. 93° C.

Workup

filtrationfiltered through a bed of silica gel
washThe filtrate is washed 8 times with water
dry with materialthe organic layer is dried with anhydrous magnesium sulfate
customthe solvents are removed in vacuo
customThe residue is purified by a flash silica gel chromatography

Sources & evidence

ORD record: ord-77bfad3b4f4648d9b1f26086e1bc5bf5
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981437

Reaction notes

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