HCID 58303869, compound → HCID 58303860, compound

HRID 1404104Notes

Reaction equation

HRID 1404104 reaction equation
C([O:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:12][N:13]2[CH3:19])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[Si:23]([O:22][CH2:21][CH2:20][C:11]1[C:10]2[C:9]([OH:8])=[C:17]([F:18])[CH:16]=[CH:15][C:14]=2[N:13]([CH3:19])[CH:12]=1)([C:26]([CH3:28])([CH3:29])[CH3:27])([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 58303869HCID 58303869, compound

Product 1

HCID 58303860HCID 58303860, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 17-4 (454 mg, 1.098 mmol) and Pd(OH)2/C in MeOH (0.5 mL NH3) was hydrogenated at ambient pressure for 30 min at 25° C., then the mixture was filtered through a plug of Celite and washed with EtOAc. The crude product was purified by column chromatography on silica gel eluting with Hexane/EtOAc (20%) to afford a white solid 17-5 in 94% yield (334 mg). 1H NMR (300 MHz, CDCl3) δ (ppm) 8.27 (br, 1H), 6.96 (dd, J=10.9, 8.8 Hz, 1H), 6.73 (s, 1H), 6.68 (dd, J=8.8, 3.3 Hz, 1H), 3.90 (t, J=5.2 Hz, 2H), 3.67 (s, 3H), 3.07 (t, J=5.5 Hz, 2H), 0.84 (s, 9H), 0.01 (s, 6H). LRMS: calc 323.2 and found: 324.2 [M+1].

Workup

  1. filtrationthe mixture was filtered through a plug of Celite
  2. washwashed with EtOAc
  3. customThe crude product was purified by column chromatography on silica gel eluting with Hexane/EtOAc (20%)

Sources & evidence

ORD record
ord-4c4d5666850b457fbaa96414dcd163c5
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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