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

HRID 62244Notes

Reaction equation

HRID 62244 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-541c623966954add8d1ca72ad697f916
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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