(E)-6-methoxy-5-morpholino-2-((6-(trifluoromethyl)pyridin-3-yl)methylene)-2,3-dihydro-1H-inden-1-one → 6-methoxy-5-morpholino-2((6-(trifluoromethyl)pyrdin-3-yl)methyl)-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:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CO.[Pd]>[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]=[N:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:5][C:4]=1[N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Compound 70 (55 mg, 0.136 mmol) was dissolved in methanol 20 mL, Pd/C 35 mg added, and the reaction stirred under hydrogen balloon for 6 h. The reaction was filtered through celite bed and washed with excess methanol. The organic layer was concentrated to get the crude compound 71. The crude 71 was purified by flash chromatography using 100-200 mesh silica gel. The compound was eluted at 28% ethyl acetate in hexane as half white coloured solid compound 6-methoxy-5-morpholino-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-2,3-dihydro-1H-inden-1-one 71. 1HNMR (400 MHz, CDCl3) δ ppm 8.61 (s, 1H), 7.74 (d, 1H), 7.59 (d, 1H), 7.17 (s, 1H), 6.80 (s, 1H), 3.89 (m, 3H), 3.86 (m, 4H), 3.39 (dd, 1H), 3.17 (m, 4H), 3.11 (m, 1H), 2.98 (m, 1H), 2.83 (m, 1H), 2.71 (m, 1H); MS (ESI) m/z 407.0 (M+H).
Workup
- filtrationThe reaction was filtered through celite bed
- washwashed with excess methanol
- concentrationThe organic layer was concentrated
Sources & evidence
- ORD record
- ord-b6964f0ddedf4fa8b35af79e0a0b06c9
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359315B2
Reaction notes
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