Boron tribromide → 2-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamide

HRID 598775Notes

Reaction equation

[CH:1]1([NH:7][C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=3)[N:12]=[C:13]([CH3:15])[CH:14]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([NH:7][C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[N:12]=[C:13]([CH3:15])[CH:14]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 2-(4-methoxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamide (630 mg, 2.01 mmol) in methylene chloride (30 mL) at −40° C. was added boron tribromide (6 mL, 1 M in DCM, 6 mmol). After the reaction was stirred at −40° C. for 10 minutes and at room temperature for 2 hours, it was quenched with saturated sodium bicarbonate. Ethyl acetate was added, and the mixture was stirred for 1 hour. The layers were separated, and the aqueous layer was extracted an additional time with ethyl acetate. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated to give 600 mg of the title compound which was used in the next reaction without further purification. LC-MS (C17H21N3O2 calculated 299) m/z 300 (M+H).

Workup

customit was quenched with saturated sodium bicarbonate
additionEthyl acetate was added
stirringthe mixture was stirred for 1 hour
customThe layers were separated
extractionthe aqueous layer was extracted an additional time with ethyl acetate
washThe combined organic layers were washed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-f997ebd08aaa4107b7a60e3e05fceeb5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897634B2

Reaction notes

Loading…