Triethylamine → (RS)-1-(2-azido-propyl)-7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrole

HRID 264573Notes

Reaction equation

HRID 264573 reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[CH:24]=[C:23]2[C:11]([CH2:12][C:13]3[CH:17]=[C:16]([CH3:18])[N:15]([CH2:19][CH:20](O)[CH3:21])[C:14]=32)=[CH:10][CH:9]=1.C(N(CC)CC)C.[N-:32]=[N+:33]=[N-:34].[Na+]>ClCCl.CN(C)C=O.O>[N:32]([CH:20]([CH3:21])[CH2:19][N:15]1[C:16]([CH3:18])=[CH:17][C:13]2[CH2:12][C:11]3[C:23]([C:14]1=2)=[CH:24][C:8]([O:7][CH3:6])=[CH:9][CH:10]=3)=[N+:33]=[N-:34]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 19036536(RS)-1-(7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

Product 1

HCID 19036468(RS)-1-(2-azido-propyl)-7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrroleYield 62.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.81 ml of methanesulfonyl chloride was added dropwise while is stirring to a solution, cooled to 0°, of 1.35 g of (RS)-1-(7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 2.9 ml of triethylamine in 40 ml of dichloromethane. The reaction mixture was subsequently added to 70 ml of water, extracted twice with 100 ml of dichloromethane each time and the combined organic phases were washed once with 70 ml of saturated sodium hydrogen carbonate solution and once with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 40 ml of anhydrous dimethylformamide, treated with 0.68 g of sodium azide and the reaction mixture was heated to 80° while stirring for 23 hours. After cooling the solution was poured into 70 ml of water and extracted twice with 100 ml of ethyl acetate each time. The combined organic phases were washed once with 70 ml of water and once with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (toluene). 0.93 g (62%) of (RS)-1-(2-azido-propyl)-7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrole was obtained as a colorless oil.

Workup

  1. extractionextracted twice with 100 ml of dichloromethane each time
  2. washthe combined organic phases were washed once with 70 ml of saturated sodium hydrogen carbonate solution and once with 70 ml of saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in a vacuum
  5. customThe brown oil obtained
  6. temperaturethe reaction mixture was heated to 80°
  7. stirringwhile stirring for 23 hours
  8. temperatureAfter cooling the solution
  9. extractionextracted twice with 100 ml of ethyl acetate each time
  10. washThe combined organic phases were washed once with 70 ml of water and once with 70 ml of saturated sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. concentrationthe solution was concentrated in a vacuum
  13. customThe brown oil obtained
  14. customwas purified by column chromatography on silica gel (toluene)

Sources & evidence

ORD record
ord-b15d0eb42b5a44e19a3768fa2f5eb30d
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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