(E)-4-chloro-5-methoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one → HCID 117940144, compound

HRID 2199836Notes

Reaction equation

HRID 2199836 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4]/[C:5](=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)/[C:6]2=[O:13]>CO>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]([F:23])([F:24])[F:25])=[CH:17][CH:16]=1)[C:6]2=[O:13]

Participants

3

Reactant 1

HCID 117940234(E)-4-chloro-5-methoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 117940144HCID 117940144, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The (E)-4-chloro-5-methoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one 176 (75 mg, 0.195 mmol) was dissolved in methanol 25 ml to which was added Pt/c 40 mg and the reaction stirred under H2 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 final compound 177 was eluted at 20% ethylacetate in hexane as half white coloured solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.69 (d, 1H), 7.58 (d, 2H), 7.29 (d, 2H), 6.98 (d, 1H), 3.99 (s, 3H), 3.38 (dd, 1H), 3.18 (dd, 1H), 2.99 (m, 1H), 2.73 (m, 1H); MS-ES+386.8.

Workup

  1. additionwas added Pt/c 40 mg
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with excess methanol
  4. concentrationThe organic layer was concentrated
  5. customto get the crude, which
  6. customwas purified by flash chromatography
  7. washThe final compound 177 was eluted at 20% ethylacetate in hexane as half white coloured solid

Sources & evidence

ORD record
ord-4b68beb92edf4ffd8d391263418a0ab1
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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