HCID 117940106, compound → HCID 117940114, compound

HRID 62273Notes

Reaction equation

HRID 62273 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[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]>[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[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[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=2)[C:6]1=[O:22]

Participants

4

Reactant 1

HCID 117940106HCID 117940106, compound

Product 1

HCID 117940114HCID 117940114, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 157 (100 mg, 0.228 mmol) was dissolved in methanol and Pd/C (40 mg) added, the reaction stirred under hydrogen balloon for 6 h, filtered through celite bed and washed with excess methanol. The organic layer was concentrated to get the crude compound 158 which was purified by flash chromatography using 100-200 mesh silica gel. The compound was eluted at 10% ethyl acetate in hexane as half white coloured solid 2-(2-chloro-5-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 158. 1HNMR (400 MHz, CDCl3) δ ppm 7.43 (m, 3H), 7.20 (s, 1H), 6.84 (s, 1H), 3.89 (m, 7H), 3.54 (dd, 1H), 3.14 (m, 4H), 3.07 (m, 2H), 2.75 (m, 2H); 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

Sources & evidence

ORD record
ord-cfe873ec5e93433e9cfa9bb4e7a73302
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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