Ethanol → HCID 58201220, compound

HRID 1944453Notes

Reaction equation

HRID 1944453 reaction equation
[C:1]1([S:7]([C:10]2[C:11]([CH2:18][C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[N:21]([CH2:29][C:30]([OH:32])=[O:31])[C:20]=3[CH3:33])=[N:12][C:13](SC)=[N:14][CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C>[Ni].O>[C:1]1([S:7]([C:10]2[C:11]([CH2:18][C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=4)[N:21]([CH2:29][C:30]([OH:32])=[O:31])[C:20]=3[CH3:33])=[N:12][CH:13]=[N:14][CH:15]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 67044091HCID 67044091, compound

Product 1

HCID 58201220HCID 58201220, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of [3-(5-benzenesulfonyl-2-methylsulfanylpyrimidin-4-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid (0.20 g), ethanol (12 mL) and water (12 mL) was treated with Raney Nickel 2800 (0.050 g), and the resulting reaction mixture was stirred at 60° C. for 45 minutes. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume) to afford the title compound as an off-white solid (0.058 g).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative reverse-phase HPLC
  5. washeluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume)

Sources & evidence

ORD record
ord-f30ff7c10a6f40b6be4b30774ced43e6
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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