N-bromobutanimide → 3-Bromo-6-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole

HRID 1477350노트

반응식

HRID 1477350 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)Cl>[Br:29][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([F:1])=[CH:3][CH:4]=3

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 867279583-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole

생성물 1

HCID 867279573-Bromo-6-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole수율 84%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 3-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole (1.06 g, 3.71 mmol) in chloroform (20 ml) was added NBS (0.66 g, 3.71 mmol) batch-wise in an ice-water bath. After complete addition, the reaction mixture was allowed to warm to room temperature slowly and stirred overnight. The reaction mixture was washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give compound 6 in 84% yield. 1H NMR (400 MHz, CDCl3) δ 8.09-8.06 (m, 1H), 7.63-7.60 (m, 1H), 7.52-7.50 (m, 1H), 7.36-7.26 (m, 2H), 7.21-7.16 (m, 1H), 4.40 (d, J=5.6 Hz, 2H), 3.82-3.80 (m, 2H), 3.49-3.46 (m, 2H), 3.40-3.38 (m, 2H), 3.29 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 158.7, 156.3, 140.1, 137.4, 128.9, 124.2, 124.2, 123.2, 122.3, 122.2, 114.4, 114.1, 111.8, 110.8, 110.0, 109.9, 106.2, 106.0. HRMS (MALDI-TOF) m/z Calcd for C17H17BrFNO2 366.0499. Found 366.0502[M]+.

후처리

  1. additionAfter complete addition
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d9810d8b9c76439ea9df73667416d07b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403794B2

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