Water → HCID 131736189, compound

HRID 1052533Notes

Reaction equation

HRID 1052533 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.Cl[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22].O>CN(C)C=O>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 158688476-Chloro-4-nitro-1H-indole

Product 1

HCID 131736189HCID 131736189, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.17 g, 6.61 mmol) was suspended in 30 mL dimethylformamide. The mixture was stirred for 15 min and was cooled at 0° C. with an ice bath. 6-Chloro-4-nitro-1H-indole (1 g, 5.09 mmol) dissolved in 5 mL dimethylformamide was added dropwise and the mixture was stirred 30 min. At the same temperature [2-(chloromethoxy)ethyl](trimethyl)silane (1.1 g, 6.61 mmol) dissolved in 5 mL dimethylformamide was added dropwise and stirred for 30 min at 0° C. The mixture was poured into water and extracted twice with ethyl acetate. The organic were dried over sodium sulphate and concentrated under reduced pressure to give 1.82 g (100% yield) of the title compound as a yellow oil. Purity 96%.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred 30 min
  3. additionwas added dropwise
  4. stirringstirred for 30 min at 0° C
  5. extractionextracted twice with ethyl acetate
  6. dry with materialThe organic were dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52dfb74efd9940b9a0a15706e2febdbc
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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