HCID 117940156, compound → HCID 117940109, compound

HRID 62238Notes

Reaction equation

HRID 62238 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1/[CH:4]=[C:5]1/[C:6](=[O:22])[C:7]2[C:12]([CH2:13]/1)=[CH:11][C:10]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[C:9]([O:20][CH3:21])[CH:8]=2>CO.[Pd]>[F:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[CH2:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:20][CH3:21])=[C:10]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH:11]=2)[C:6]1=[O:22]

Participants

4

Reactant 1

HCID 117940156HCID 117940156, compound

Product 1

HCID 117940109HCID 117940109, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 27 (45 mg, 0.121 mmol), dissolved in methanol, was added Pd/C 20 mg and 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 was eluted at 23% ethyl acetate in hexane as half white coloured solid compound 2-(2,4-difluorobenzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 28. 1HNMR (400 MHz, CDCl3) δ ppm 7.18 (m, 2H), 6.82 (m, 3H), 3.88 (m, 3H), 3.86 (m, 4H), 3.31 (m, 1H), 3.16 (m, 4H), 3.06 (m, 1H), 2.95 (m, 1H), 2.73 (m, 2H); MS (ESI) m/z 373.9 (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 was eluted at 23% ethyl acetate in hexane as half white coloured solid compound 2-(2,4-difluorobenzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 28

Sources & evidence

ORD record
ord-22566f14645a4bc2aa527ef8c4986e0c
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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