N-Methylethylenediamine → 2-(3-Bromo-2-methylphenyl)-9-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one

HRID 1918829ノート

反応式

HRID 1918829 の反応式
[CH3:1][Si:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2[CH2:16][CH2:17][NH:18][C:19](=[O:20])[C:8]1=2.[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](Br)[C:25]=1[CH3:31].C(=O)([O-])[O-].[Cs+].[Cs+].CNCCN>[Cu](I)I.O1CCOCC1>[Br:23][C:24]1[C:25]([CH3:31])=[C:26]([N:18]2[CH2:17][CH2:16][C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:22])([CH3:21])[CH3:1])[C:8]=3[C:19]2=[O:20])[CH:27]=[CH:28][CH:29]=1

参加物

7

反応物 4

HCID 8014N-MethylethylenediamineHCID 10796Cesium carbonateHCID 346812,6-DibromotolueneHCID 10358416HCID 10358416、化合物

生成物 1

HCID 580436472-(3-Bromo-2-methylphenyl)-9-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one収率 41%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with 117a (400 mg, 1.27 mmol), 2,6-dibromotoluene (633 mg, 2.53 mmol), cesium carbonate (828 mg, 2.54 mmol), N-methylethylenediamine (112 mg, 1.27 mmol) and 1,4-dioxane (20 mL). After bubbling nitrogen through the resulting suspension for 30 min, copper iodide (121 mg, 2.54 mmol) was added. A reflux condenser was attached to the flask, and the reaction mixture was heated at 100° C. for 16 h. After this time, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by flash column to afford 117b in 41% yield (251 mg) as a yellow oil: 1H NMR (500 MHz, CDCl3) d 7.71 (d, 1H, J=8.0 Hz), 7.68 (d, 1H, J=8.0 Hz), 7.63 (d, 1H, J=8.0 Hz), 7.47 (t, 1H, J=8.0 Hz), 7.32-7.28 (m, 2H), 7.21 (t, 1H, J=8.0 Hz), 6.13 (s, 2H), 4.15 (m, 1H), 3.93 (m, 1H), 3.69 (m, 2H), 3.29 (m, 2H), 2.45 (s, 3H), 0.95 (t, 2H, J=8.0 Hz), −0.07 (s, 9H).

後処理

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. customAfter bubbling nitrogen through the resulting suspension for 30 min
  3. customA reflux condenser was attached to the flask
  4. temperatureAfter this time, the mixture was cooled to room temperature
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by flash column

出典と根拠

ORDレコード
ord-e74d71a0508246b4a8d268f683b23b01
出典データセット
uspto-grants-2013_12
特許番号
US08618107B2

反応ノート

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