Dichloromethane → HCID 59238889、化合物

HRID 2060988ノート

反応式

HRID 2060988 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, 2H), 8.39 (dd, J=10.0, 2.4 Hz, 2H), 7.55 (dd, J=8.8, 4.4 Hz, 2H), 7.31 (td, J=8.8, 2.4 Hz, 2H), 4.34 (t, J=5.2 Hz, 2H), 2.74 (t, J=5.6 Hz, 2H), 2.36 (s, 6H); 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-88649d70d4924cdcad4be2332dbdda71
出典データセット
uspto-grants-2012_10
特許番号
US08278341B2

反応ノート

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