Methanol → HCID 121370999, compound

HRID 2199803Notes

Reaction equation

HRID 2199803 reaction equation
CO[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7]/[C:8](=[CH:13]\[C:14]3[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[CH3:30][OH:31]>[Pd]>[CH3:30][O:31][C:8]1([CH2:13][C:14]2[C:19]([C:20]([F:21])([F:23])[F:22])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:7][C:6]2[C:10](=[CH:11][CH:3]=[C:4]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH:5]=2)[C:9]1=[O:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 117940089(E)-6-methoxy-5-morpholino-2-((3-(trifluoromethyl)pyridin-2-yl)methylene)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 121370999HCID 121370999, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Compound 67 (80 mg, 0.197 mmol) was dissolved in methanol 15 mL, Pd/C 50 mg added, and the reaction 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. The crude was purified by flash chromatography using 100-200 mesh silica gel. The compound was eluted at 26% ethyl acetate in hexane as half white coloured solid compound 68. 1HNMR (400 MHz, CDCl3) δ ppm 8.64 (d, 1H), 7.91 (d, 1H), 7.22 (d, 2H), 6.83 (s, 1H), 3.89 (m, 7H), 3.65 (dd, 1H), 3.44 (m, 1H), 3.16 (m, 6H), 2.72 (dd, 1H); MS (ESI) m/z 407.0 (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
  5. customThe crude was purified by flash chromatography
  6. washThe compound was eluted at 26% ethyl acetate in hexane as half white coloured solid compound 68

Sources & evidence

ORD record
ord-3eb3a799c0444c8d916ca6fd4856ca69
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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