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

HRID 659650

반응식

HRID 659650 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-741079cb9409415294e964e2612c158c
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080566B1

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