Triethylamine → HCID 68667503, compound

HRID 216371Notes

Reaction equation

C(N(S(F)(F)[F:7])CC)C.[CH3:10][C:11]([CH3:54])([CH2:52][CH3:53])[CH2:12][C:13]1[N:14]=[C:15]([CH2:37][CH:38]([C:40]2[CH:45]=[CH:44][C:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)=[CH:42][CH:41]=2)O)[N:16]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:10][C:11]([CH3:54])([CH2:52][CH3:53])[CH2:12][C:13]1[N:14]=[C:15]([CH2:37][CH:38]([C:40]2[CH:45]=[CH:44][C:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=3)=[CH:42][CH:41]=2)[F:7])[N:16]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diethylaminosulfur trifluoride (0.1 mL, 0.78 mmol) was added to a 0° C. solution of 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-(4-pyridin-2-ylphenyl)ethanol (385 mg, 0.65 mmol) in methylene chloride (10 mL). After stirring at 0° C. for 30 min then warming to ambient temperature then letting sit at −20° C. overnight, triethylamine (1 mL) was added. After stirring for a further 5 min, the reaction mixture was concentrated in vacuo. Chromatography over silica eluting with 0-40% ethyl acetate/hexane afforded 2-(4-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-fluoroethyl}phenyl)pyridine.

Workup

temperaturethen warming to ambient temperature
waitthen letting sit at −20° C. overnight
stirringAfter stirring for a further 5 min
concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-2434329bd32d4a648f4efb61600c469c
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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