HCID 67251961, compound → HCID 57949795, compound

HRID 2427544Notes

Reaction equation

HRID 2427544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:25]2[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH:30]=2)[CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[CH2:8]2.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]2[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]2)[CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:18][CH:19]=1)[CH2:8]2

Participants

5

Reactant 2

HCID 67251961HCID 67251961, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57949795HCID 57949795, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Methoxy-5-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (17 mg, 0.040 mmol) was stirred in methanol for 20 minutes under argon before a small scoop of palladium on carbon was added and the reaction atmosphere was changed to hydrogen. The reaction was allowed to stir for 18 hours under hydrogen. The reaction was filtered and the solvent was removed under reduced pressure to yield 7.2 mg (42%) of a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.35 (d, 2H), 7.16 (d, 2H), 6.74 (d, 2H), 4.74 (s, 2H), 4.20 (s, 2H), 3.98 (s, 3H), 3.50 (s, 2H), 2.98-3.01 (m, 2H), 2.53-2.60 (m, 1H), 2.04-2.11 (m, 2H), 1.75-1.87 (m, 5H).

Workup

  1. additionwas added
  2. customthe reaction atmosphere
  3. filtrationThe reaction was filtered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-332992cd64774ee38150ec5f3bad455b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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