(E)-2-(3-bromo-2,6-difluorobenzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one → 2, 6-difluorobenzyl-6-methoxy-5-morpholino-2, 3-dihydro-1H-inden-1-one

HRID 2199797Notes

Reaction equation

HRID 2199797 reaction equation
Br[C:2]1[C:3]([F:28])=[C:4]([C:24]([F:27])=[CH:25][CH:26]=1)/[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>CO.[Pd]>[F:27][C:24]1[CH:25]=[CH:26][CH:2]=[C:3]([F:28])[C:4]=1[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 117940382(E)-2-(3-bromo-2,6-difluorobenzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 1179400262, 6-difluorobenzyl-6-methoxy-5-morpholino-2, 3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 41 (40 mg, 0.088 mmol) was dissolved in methanol 15 mL and added Pd/C 20 mg and stirred under hydrogen balloon for 6 h. The reaction was filtered through elite bed and washed with excess methanol. The organic layer was concentrated to get the crude compound 42, which was purified by flash chromatography using 100-200 mesh silica gel. The compound 2-(2,6-difluorobenzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 42 was eluted as des-brominated compound at 26% ethyl acetate in hexane as half white coloured solid. 1HNMR (400 MHz, CDCl3) δ ppm 7.17 (m, 2H), 6.89 (m, 3H), 3.89 (m, 7H), 3.35 (m, 1H), 3.19 (m, 4H), 3.06 (m, 2H), 2.76 (m, 2H); MS (ESI) m/z 374.0 (M+H).

Workup

  1. filtrationThe reaction was filtered through elite bed
  2. washwashed with excess methanol
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-4490921ab13c466d9fcaaa93a40bf801
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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