Water → HCID 117798739, compound

HRID 1497379Notes

Reaction equation

HRID 1497379 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:22]=[CH:21][C:20]4[C:16](=[C:17]([CH3:26])[N:18]([CH2:23][CH2:24][OH:25])[N:19]=4)[CH:15]=3)[C:10](=[O:27])[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:33][CH2:34][O:35][CH3:36].O>CN(C)C=O>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:22]=[CH:21][C:20]4[C:16](=[C:17]([CH3:26])[N:18]([CH2:23][CH2:24][O:25][CH2:33][CH2:34][O:35][CH3:36])[N:19]=4)[CH:15]=3)[C:10](=[O:27])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 118534015HCID 118534015, compound

Product 1

HCID 117798739HCID 117798739, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(4-chlorobenzyl)oxy]-1-[2-(2-hydroxyethyl)-3-methyl-2H-indazol-5-yl]pyridin-2(1H)-one (30 mg) in N,N-dimethylformamide (2 ml) was added 60% sodium hydride (3.51 mg) at 0° C., and the mixture was stirred at room temperature for 30 min. To the obtained reaction mixture was added (2-bromoethyl)methyl ether (15.3 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (28.1 mg).

Workup

  1. customTo the obtained reaction mixture
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d3696cb22902479bb09e66be5aaf8c72
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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