(E)-2-(5-chloro-2-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one → HCID 117940095, compound

HRID 2199801Notes

Reaction equation

HRID 2199801 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:27]([F:30])([F:29])[F:28])=[C:6]([CH:26]=1)/[CH:7]=[C:8]1/[C:9](=[O:25])[C:10]2[C:15]([CH2:16]/1)=[CH:14][C:13]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[C:12]([O:23][CH3:24])[CH:11]=2>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:27]([F:29])([F:28])[F:30])=[C:6]([CH:26]=1)[CH2:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:23][CH3:24])=[C:13]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:14]=2)[C:9]1=[O:25]

Participants

4

Reactant 1

HCID 117940155(E)-2-(5-chloro-2-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 117940095HCID 117940095, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 52 (50 mg, 0.114 mmol) was dissolved in methanol 30 mL, Pd/C 17 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, which was purified by flash chromatography using 100-200 mesh silica gel. The compound 53 was eluted at 24% ethyl acetate in hexane as half white coloured solid compound 2-(5-chloro-2-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 53. 1HNMR (400 MHz, CDCl3) δ ppm 7.43 (m, 3H), 7.18 (s, 1H), 6.82 (s, 1H), 3.90 (m, 3H), 3.87 (m, 4H), 3.48 (d, 1H), 3.38 (m, 1H), 3.17 (m, 4H), 3.09 (m, 1H), 2.95 (m, 1H), 2.67 (m, 2H); MS (ESI) m/z 440.0 (M+H).

Workup

  1. filtrationThe reaction was filtered through celite bed
  2. washwashed with excess methanol
  3. concentrationThe organic layer was concentrated
  4. customto get the crude, which
  5. customwas purified by flash chromatography
  6. washThe compound 53 was eluted at 24% ethyl acetate in hexane as half white coloured solid compound 2-(5-chloro-2-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 53

Sources & evidence

ORD record
ord-6001e71295534540aa8a43e026179b73
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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