HCID 117940033, compound → HCID 117940099, compound

HRID 2199846Notes

Reaction equation

HRID 2199846 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([C:9]1[CH:10]=[C:11](/[CH:15]=[C:16]2/[C:17](=[O:33])[C:18]3[C:23]([CH2:24]/2)=[CH:22][C:21]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[C:20]([O:31][CH3:32])[CH:19]=3)[CH:12]=[N:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]>CO.[Pd]>[F:34][C:2]([F:1])([F:35])[C:3]([C:9]1[CH:10]=[C:11]([CH2:15][CH:16]2[CH2:24][C:23]3[C:18](=[CH:19][C:20]([O:31][CH3:32])=[C:21]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:22]=3)[C:17]2=[O:33])[CH:12]=[N:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

4

Reactant 1

HCID 117940033HCID 117940033, compound

Product 1

HCID 117940099HCID 117940099, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 263 (50 mg, 0.090 mmol) was dissolved in methanol 25 ml, Pd/C 40 mg added, 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 crude compound 264 was eluted at 20% ethyl acetate in hexane as half white coloured solid 2-((5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-3-yl)methyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 264.

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, which
  5. customwas purified by flash chromatography
  6. washThe crude compound 264 was eluted at 20% ethyl acetate in hexane as half white coloured solid 2-((5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-3-yl)methyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 264

Sources & evidence

ORD record
ord-066bcf5674864b8b81d5a435297c4092
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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