(E)-6-methoxy-5-(4-methylpiperidin-1-yl)-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one → 6-methoxy-5-(4-methylpiperidin-1-yl)-2-(4-((trifluoromethyl)thio)benzyl)-2,3-dihydro-1H-inden-1-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7]/[C:8](=[CH:13]\[C:14]3[CH:19]=[CH:18][C:17]([S:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:25]1[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]1>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([S:20][C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:5][C:4]=1[N:25]1[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The 139 (80 mg, 0.178 mmol) was dissolved in methanol 50 mL and Raney-Nickel (8 mg) added and the reaction stirred under hydrogen balloon for 2 h. The reaction was filtered through celite bed and washed with excess methanol. The organic layer was concentrated to get the crude compound 140 and purified by flash chromatography using 100-200 mesh silica gel. The compound 140 was eluted at 8% ethyl acetate in hexane as half white coloured solid compound 6-methoxy-5-(4-methylpiperidin-1-yl)-2-(4-((trifluoromethyl)thio)benzyl)-2,3-dihydro-1H-inden-1-one 140. 1HNMR (400 MHz, CDCl3) δ ppm 7.27 (m, 3H), 7.11 (m, 4H), 6.81 (s, 1H), 3.89 (s, 3H), 3.60 (bs, 2H), 3.37 (dd, 1H), 2.94 (m, 2H), 2.59 (m, 4H), 0.94 (m, 3H), 0.86 (m, 4H); MS (ESI) m/z 450.1 (M+H).
Workup
- filtrationThe reaction was filtered through celite bed
- washwashed with excess methanol
- concentrationThe organic layer was concentrated
Sources & evidence
- ORD record
- ord-b0deee7d2e8543cdbf5494e631e050ec
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359315B2
Reaction notes
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