Sodium hydride → HCID 19750836, compound

HRID 484103Notes

Reaction equation

HRID 484103 reaction equation
[CH3:1][S:2]([C:5]1[C:6]2[C:7]3[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]=3[CH:15]=[CH:16][CH:17]=2)(=[O:4])=[O:3].[H-].[Na+].Br[CH2:21][CH:22]1[CH2:24][CH2:23]1>CN(C)C=O>[CH:22]1([CH2:21][N:10]2[C:11]3[C:7]4[C:6](=[CH:17][CH:16]=[CH:15][C:8]=4[C:9]2=[O:14])[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][CH:12]=3)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503Bromomethylcyclopropane2×HCID 10131121HCID 10131121, compound

Product 1

HCID 19750836HCID 19750836, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.5 g of 6-(methylsulfonyl)-benz[cd]indol-2(1H)-one (Example 3) in 50 ml of N,N-dimethylformamide is treated with 0.35 g of sodium hydride and 1.5 ml of (bromomethyl)cyclopropane at 75° C. in a pressure bottle for 24 hours. An additional 1.5 ml of (bromomethyl)cyclopropane is added and heating continued at 75° C. for 17 hours in a pressure bottle. The reaction mixture is cooled then evaporated. The concentrate is chromatographed on silica gel using 1:1 ethyl acetate-hexane to afford 0.72 g of the desired product as yellow crystals, m.p. 148°-150° C.

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture is cooled
  3. customthen evaporated
  4. customThe concentrate is chromatographed on silica gel using 1:1 ethyl acetate-hexane

Sources & evidence

ORD record
ord-6f722512409749388dff4cb71c870951
Source dataset
uspto-grants-1993_07
Patent number
US05229411

Reaction notes

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