Sodium hydride → HCID 49855107, compound

HRID 2407629Notes

Reaction equation

HRID 2407629 reaction equation
[H-].[Na+].[CH2:3]([NH:11][S:12]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH2:26][CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1>CN(C=O)C>[NH:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28]([CH2:27][CH2:26][N:11]([CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:29]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 769243-(2-Bromoethyl)indoleHCID 3740335HCID 3740335, compound

Product 1

HCID 49855107HCID 49855107, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Under inert atmosphere, to a stirred solution of NaH (0.016 g, 0.36 mmol) in 0.20 ml anhydrous DMF at 0° C., was added a solution of compound of Example 2 (0.108 g, 0.35 mmol) in 0.60 ml anhydrous DMF. The temperature was maintained during 1.5 h. After this time, a solution of 3-(2-Bromoethyl)indole (0.088 g, 0.39 mmol) in 0.6 anhydrous DMF was added dropwise to the reaction mixture of step at 0° C., and was stirred during 2.5 h. Once the solvent was evaporated, the crude mixture was chromatographically purified over SiO2 using Hexane/AcOEt (70:30) as the eluant, furnishing 133 mg of the desired product in 84% yield (purity ≧80%, expressed in % HPLC area).

Workup

  1. temperatureThe temperature was maintained during 1.5 h
  2. customOnce the solvent was evaporated
  3. customthe crude mixture was chromatographically purified over SiO2

Sources & evidence

ORD record
ord-157717a300204a378491ede292be745b
Source dataset
uspto-grants-2014_08
Patent number
US08809584B2

Reaction notes

Loading…