Dichloromethane → HCID 59238889, 화합물

HRID 1949117노트

반응식

HRID 1949117 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[C:8]3[NH:21][C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][C:27]=4[C:7]3=[CH:6][C:5]2=1.[Br:29]Br.C(Cl)Cl>CN(C=O)C>[Br:29][C:6]1[C:7]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)[NH:21][C:8]=2[C:9]([O:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])=[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][C:2]([F:1])=[CH:3][C:4]=3[C:5]=12

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 24408BromineHCID 45138929HCID 45138929, 화합물

생성물 1

HCID 59238889HCID 59238889, 화합물수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-dimethylethanamine (213.9 mg, 0.5638 mmol) in DMF (20 mL) at 0° C. was added Br2 in CH2Cl2 (50 mg/mL, 1.982 mL, 0.6201 mmol). The reaction was warmed to room temperature and stirred for two hours. DMF was removed via vacuum pump. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aq. NaCO3. The organic layers was concentrated and subjected to flash chromatography to provide the title compound (188.4 mg, 73%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.89 (br s, 2 H), 8.39 (dd, J=10.0, 2.4 Hz, 2 H), 7.55 (dd, J=8.8, 4.4 Hz, 2 H), 7.31 (td, J=8.8, 2.4 Hz, 2 H), 4.34 (t, J=5.2 Hz, 2 H), 2.74 (t, J=5.6 Hz, 2 H), 2.36 (s, 6 H); MS (ESI) m/z 456.1 (M−H)−; MS (ESI) m/z 458.0 (M+H)+

후처리

  1. customDMF was removed via vacuum pump
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated aq. NaCO3
  4. concentrationThe organic layers was concentrated

출처 및 근거

ORD 기록
ord-2db37d0b91ff4ad2bbf3f8e9a9522211
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399502B2

반응 노트

불러오는 중…