N-bromobutanimide → diethyl 5-bromo-2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate

HRID 350815노트

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HRID 350815 반응식
[CH3:1][CH:2]1[CH2:11][N:10]2[CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH:13]3[C:8]3[C:9]2=[C:4]([CH:5]=[CH:6][CH:7]=3)[N:3]1[C:23]([O:25][CH2:26][CH3:27])=[O:24].C1C(=O)N([Br:35])C(=O)C1>CN(C=O)C.O>[Br:35][C:6]1[CH:7]=[C:8]2[CH:13]3[CH2:14][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17][CH:12]3[N:10]3[CH2:11][CH:2]([CH3:1])[N:3]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:4]([CH:5]=1)=[C:9]23

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 22036784diethyl 2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate

생성물 1

HCID 22036791diethyl 5-bromo-2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate수율 88.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution of diethyl 2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (40 mg, 0.1 mmol) in DMF (10 mL) at 0° C. was added NBS (20 mg, 0.11 mmol) and stirred at 0° C. for 2 hours. The solution was diluted with water (10 mL), and extracted with EtOAc (2×20 mL). The combined extracts were dried over magnesium sulfate, concentrated, and purified by flash chromatography to afford diethyl 5-bromo-2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (40 mg, 88%) as a clear oil. MS [M+H]+ 454.

후처리

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. concentrationconcentrated
  4. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-235f1549202f4ca882a93c7717e0ebe0
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183282B2

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