HCID 178435254, compound → HCID 21106103, compound

HRID 1354575Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([C:13]2([CH2:23][CH3:24])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([F:22])[CH:19]=3)[CH2:14]2)=[CH:11][N:10]=[C:9]1S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Ni]>[CH2:1]([N:8]1[C:12]([C:13]2([CH2:23][CH3:24])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([F:22])[CH:19]=3)[CH2:14]2)=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

7.5 ml of Raney-Nickel prepared according to Vogel, Practical Organic Chemistry, 5th Edition, 1999, Longman, U.K. p. 450–451, was mixed with 20 ml of ethanol under nitrogen atmosphere in a round-bottomed flask equipped with a thermometer and a stirring bar. 500 mg of 1-benzyl-5-(2-ethyl-5-fluoro-indan-2-yl)-imidazole-2-thiol was dissolved in 10 ml of ethanol and added to the mixture. The reaction mixture was stirred at 40° C. for about 10 hours and then the temperature was raised to 60° C. for 2 hours followed by cooling to room temperature. The mixture was filtered and the filter (Celite™) was washed with ethanol. The ethanol solution was evaporated to dryness to obtain 151 mg of a crude product. After chromatographic purification using methylene chloride, methylene chloride:methanol (10:1) and methylene chloride:methanol (1:1) as eluents 1-benzyl-5-(2-ethyl-5-fluoro-indan-2-yl)-imidazole was obtained. The purity was measured by HPLC: 83%.

Workup

customequipped with a thermometer and a stirring bar
additionadded to the mixture
temperaturethe temperature was raised to 60° C. for 2 hours
temperatureby cooling to room temperature
filtrationThe mixture was filtered
filtrationthe filter (Celite™)
washwas washed with ethanol
customThe ethanol solution was evaporated to dryness

Sources & evidence

ORD record: ord-e7e25f21c9f4439e940063b56b6a7102
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223871B2

Reaction notes

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