5-[4-(Benzyloxy)phenyl]-1-cyclohexyl-3-(2,2-dibromovinyl)-1H-pyrazole → 5-[4-(benzyloxy)phenyl]-1-cyclohexyl-3-ethynyl-1H-pyrazole

HRID 2216519Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:23]=[C:22]([CH:31]=[C:32](Br)Br)[CH:21]=2)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[N:23]=[C:22]([C:31]#[CH:32])[CH:21]=2)=[CH:16][CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: -50 °C

Procedure

n-Butyllithium (1.6 M BuLi in hexanes, 1.65 ml, 2.64 mmol) was added dropwise to a solution of 7.1 (620 mg, 1.20 mmol) in THF (6 ml) at −50°. The mixture was stirred at −50° C. for 30 min, quenched with H2O, diluted with EtOAc, washed with 1N HCl, H2O, brine, and dried (Na2SO4). The crude product was purified by SiO2 chromatography to afford 261 mg (61%) of 7.2. MS (ESI) 357.3 (MH+).

Workup

customquenched with H2O
additiondiluted with EtOAc
washwashed with 1N HCl, H2O, brine
dry with materialdried (Na2SO4)
customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record: ord-f75267424bfe491594200344707ba44f
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112601B2

Reaction notes

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