Hydrogen Peroxide → HCID 117952520, compound

HRID 1499121Notes

Reaction equation

[B]1OC2C(=CC=CC=2)O1.[F:10][C:11]([F:28])([F:27])[C:12]([C:14]1[C:15]([N:21]2[CH:25]=[CH:24][C:23]([CH3:26])=[N:22]2)=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[O:13].[OH-].[Na+].OO>C1COCC1>[F:28][C:11]([F:10])([F:27])[C@@H:12]([C:14]1[C:15]([N:21]2[CH:25]=[CH:24][C:23]([CH3:26])=[N:22]2)=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=1)[OH:13]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of (S)-(−)-2-Butyl-CBS-oxazaborolidine solution (3.0 ml 1.0 M in toluene) and catecholborane (30 ml 1.0 M in THF) was stirred at RT for 30 min. The mixture was then cooled to −70° C. and 2,2,2-trifluoro-1-(6-methyl-2-(3-methyl-1H-pyrazol-1-yl)pyridin-3-yl)ethanone (1 g, 2.9 mmol) in THF (16 mL) was added dropwise. After addition, the reaction mixture was warmed up to −32° C. and stirred for 12 h. After this time, 3N NaOH (18 mL) was added followed by H2O2 (18 mL) and the temperature of the reaction mixture was increased to RT for 30 min and then extracted with ethyl. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo and purified by normal phase silica gel column (EtOAc/hepate) to provide the title compound as a yellow solid.

Workup

additionAfter addition
temperaturethe reaction mixture was warmed up to −32° C.
temperaturethe temperature of the reaction mixture was increased to RT for 30 min
extractionextracted with ethyl
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by normal phase silica gel column (EtOAc/hepate)

Sources & evidence

ORD record: ord-023ecc99925b48c899156cf661b2d6ed
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199994B2

Reaction notes

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