HCID 52951276, compound → HCID 52951277, compound

HRID 508606Notes

Reaction equation

HRID 508606 reaction equation
[CH2:1]([O:3][C:4](=[O:28])/[CH:5]=[CH:6]/[C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[N:8]=1)[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([C:18]2[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[N:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 52951276HCID 52951276, compound

Product 1

HCID 52951277HCID 52951277, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 16 (0.17 g, 0.42 mmol) in 5 mL of EtOAc was added 10% palladium on carbon. The solution was filled with H2 and the reaction mixture was stirred for 2 hours. After the solution was filtered through Celite, the filtrate was concentrated in vacuo. Purification by column chromatography (3:7 EtOAc-hexanes) gave the title compound, 0.15 g (90%) as a white solid. mp 96.5-99.1° C. 1H NMR (300 MHz, DMSO-d6): δ 7.91 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 2H), 7.44-7.37 (m, 3H), 7.29-7.23 (m, 2H), 6.57 (s, 1H), 4.09 (q, J=7 Hz, 2H), 3.24 (s, 3H), 2.93 (t, J=7 Hz, 2H), 2.74 (t, J=7 Hz, 2H), 1.18 (t, J=7 Hz, 3H).

Workup

  1. additionThe solution was filled with H2
  2. filtrationAfter the solution was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customPurification by column chromatography (3:7 EtOAc-hexanes)

Sources & evidence

ORD record
ord-1750f1ef320149769592b11c50c00399
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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