Ethyl Bromide → methyl 9-ethyl-9H-carbazole-1-carboxylate

HRID 659650Notes

Reaction equation

HRID 659650 reaction equation
[C:1]1([C:14]([O:16][CH3:17])=[O:15])[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:21][CH3:22]>CN(C=O)C>[CH2:21]([N:12]1[C:13]2[C:1]([C:14]([O:16][CH3:17])=[O:15])=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:22]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 643304methyl 9H-carbazole-1-carboxylate

Product 1

HCID 67996321methyl 9-ethyl-9H-carbazole-1-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100-mL round-bottom flask was charged with a solution of methyl 9H-carbazole-1-carboxylate (2 g, 8.89 mmol, 1.00 equiv) in DMF (20 mL). To this was added NaH (1.78 g, 74.17 mmol, 5.00 equiv) in several batches followed by addition of bromoethane (1.92 g, 17.94 mmol, 2.00 equiv). The resulting solution was stirred at room temperature for 6 hours. Upon completion, the reaction was then quenched with water (20 mL). The mixture was then extracted with ethyl acetate (3×20 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (50:1) affording methyl 9-ethyl-9H-carbazole-1-carboxylate as light yellow solid (1.3 g, 58%).

Workup

  1. customUpon completion, the reaction was then quenched with water (20 mL)
  2. extractionThe mixture was then extracted with ethyl acetate (3×20 mL)
  3. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was purified by a silica gel column chromatography
  7. washeluted with dichloromethane/methanol (50:1)

Sources & evidence

ORD record
ord-741079cb9409415294e964e2612c158c
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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