HCID 117940169, compound → HCID 117940093, compound

HRID 2199815Notes

Reaction equation

HRID 2199815 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[C:27]([F:30])([F:29])[F:28])/[CH:5]=[C:6]1/[C:7](=[O:23])[C:8]2[C:13]([CH2:14]/1)=[CH:12][C:11]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[C:10]([O:21][CH3:22])[CH:9]=2>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[C:27]([F:28])([F:29])[F:30])[CH2:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:21][CH3:22])=[C:11]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[CH:12]=2)[C:7]1=[O:23]

Participants

4

Reactant 1

HCID 117940169HCID 117940169, compound

Product 1

HCID 117940093HCID 117940093, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 91 (220 mg, 0.502 mmol) was dissolved in ethyl acetate 150 mL, Pd/C 100 mg added, and the reaction stirred under hydrogen balloon for 6 h, then filtered through celite bed and washed with excess methanol. The organic layer was concentrated to get the crude 92 which 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 2-(3-chloro-4-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 92. 1HNMR (400 MHz, CDCl3) δ ppm 7.59 (d, 1H), 7.49 (d, 1H), 7.31 (m, 1H), 7.19 (s, 1H), 6.83 (s, 1H), 3.89 (m, 3H), 3.87 (m, 4H), 3.53 (m, 1H), 3.17 (m, 4H), 3.07 (m, 2H), 2.91 (m, 1H), 2.73 (m, 1H); MS (ESI) m/z 440.0 (M+H).

Workup

  1. filtrationfiltered through celite bed
  2. washwashed with excess methanol
  3. concentrationThe organic layer was concentrated
  4. customto get the crude 92 which
  5. customwas purified by flash chromatography
  6. washThe compound was eluted at 28% ethyl acetate in hexane as half white coloured solid compound 2-(3-chloro-4-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 92

Sources & evidence

ORD record
ord-d293b31adaf94edf9915b48d46bfd8dd
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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