HCID 21071406、化合物 → HCID 21071593、化合物

HRID 1371914ノート

反応式

HRID 1371914 の反応式
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:9]=[C:8]2[CH2:24][CH2:25][N:26]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:2][CH3:3]>CCO.O.NN>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11]([N:10]([Si:14]([CH:21]([CH3:22])[CH3:23])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:16])[CH3:17])[CH:9]=[C:8]2[CH2:24][CH2:25][NH2:26])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

参加物

4

反応物 1

HCID 21071406HCID 21071406、化合物

生成物 1

HCID 21071593HCID 21071593、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 24654Hydrazine hydrate (1:1)溶媒

実験手順

Combine 2-(2-(5-propoxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione (416 mg, 0.8 mmol) in 20 mL EtOH and 1 mL hydrazine hydrate. Reflux for 3 hours, filter through celite and concentrate to residue. Dissolve the residue in 10 mL MeOH and load onto a 12 g SCX ion exchange cartridge and rinse sequentially with MeOH, DMP, then MeOH. Elute the product with 2 M NH3 in MeOH to give the title compound as an oil: ISMS 375 (M+1); 1H NMR (CDCl3) 7.34–7.32 (d, 1H), 7.02 (s, 1H), 7.00–6.99 (d, 1H), 6.80–6.77 (m, 1H), 3.97–3.94 (m, 2H), 3.01–2.98 (m, 2H), 2.86–2.83 (m, 2H), 1.88–1.76 (m 2H), 1.70–1.58 (m, 3H), 1.3 (bs, 2H), 1.14–1.08 (m, 18H), 1.06–1.02 (t, 3H).

後処理

  1. temperatureReflux for 3 hours
  2. filtrationfilter through celite
  3. concentrationconcentrate to residue
  4. dissolutionDissolve the residue in 10 mL MeOH
  5. washload onto a 12 g SCX ion exchange cartridge and rinse sequentially with MeOH, DMP
  6. washElute the product with 2 M NH3 in MeOH

出典と根拠

ORDレコード
ord-bb2de4e5599f473d802879e110cf21d6
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

反応ノート

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