Dimethyl Sulfoxide → HCID 86730357, compound

HRID 1427056Notes

Reaction equation

HRID 1427056 reaction equation
CS(C)=O.[CH3:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][NH:17]2)=[CH:13][C:12]=1[OH:20].Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:23]=1.CC(C)([O-])C.[K+]>O.C(OCC)(=O)C>[CH3:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][NH:17]2)=[CH:13][C:12]=1[O:20][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:23]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 22832129N-(4-Chloropyridin-2-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 86730356HCID 86730356, compound

Product 1

HCID 86730357HCID 86730357, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

Dimethylsulfoxide (25 mL) was added to a mixture of 6-(3-methoxypropoxy)-1H-indol-5-ol described in Production Example 32-5 (3.81 g, 17.2 mmol), N-(4-chloropyridin-2-yl)acetamide described in Production Example 1-5 (3.23 g, 18.9 mmol), and potassium tert-butoxide (2.12 g, 18.9 mmol) under nitrogen atmosphere at room temperature. The liquid mixture was stirred at 150° C. for 14 hours. The reaction liquid was cooled to room temperature, and then ethyl acetate and water were added. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:1-0:1-ethyl acetate:methanol=49:1) to obtain the title compound (2.83 g, 46%).

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. washThe organic layer was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:1-0:1-ethyl acetate:methanol=49:1)

Sources & evidence

ORD record
ord-726b7afb01e84b58afbf32b5493739fe
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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