Dichloromethane → HCID 59238889、化合物

HRID 1949117ノート

反応式

HRID 1949117 の反応式
[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

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 24408BromineHCID 45138929HCID 45138929、化合物

生成物 1

HCID 59238889HCID 59238889、化合物収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-2db37d0b91ff4ad2bbf3f8e9a9522211
出典データセット
uspto-grants-2013_03
特許番号
US08399502B2

反応ノート

読み込み中…