HCID 117940173, compound → 2-(4-chloro-2-fluorobenzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

HRID 2199790Notes

Reaction equation

HRID 2199790 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5](/[CH:6]=[C:7]2/[C:8](=[O:24])[C:9]3[C:14]([CH2:15]/2)=[CH:13][C:12]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:11]([O:22][CH3:23])[CH:10]=3)=[C:4]([F:27])[CH:3]=1>CO.[Pd]>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH:7]2[CH2:15][C:14]3[C:9](=[CH:10][C:11]([O:22][CH3:23])=[C:12]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[CH:13]=3)[C:8]2=[O:24])=[C:4]([F:27])[CH:3]=1

Participants

4

Reactant 1

HCID 117940173HCID 117940173, compound

Product 1

HCID 1179403932-(4-chloro-2-fluorobenzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 15 (45 mg, 0.121 mmol) was dissolved in methanol and was added Pd/C 20 mg and stirred the reaction 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 16. The crude 16 was purified by flash chromatography using 100-200 mesh silica gel. Compound 16 was eluted at 23% ethyl acetate in hexane as half white coloured solid 2-(4-chloro-2-fluorobenzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 16. 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 389.8 (M+H).

Workup

  1. customthe reaction under hydrogen balloon for 6 h
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with excess methanol
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-51637341dd2b42c0b1636d9c1ccb5b01
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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