Water → 5-(2,6-Diethyl-Phenyl)-1-(1-Propyl-Butyl)-1H-Pyrrolo[2,3-C]Pyridine

HRID 602523

反応式

HRID 602523 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[H-].[Na+].Br[CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26].O>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([CH:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[C:14]2=[CH:15][N:16]=1)[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

生成物 1

HCID 116817955-(2,6-Diethyl-Phenyl)-1-(1-Propyl-Butyl)-1H-Pyrrolo[2,3-C]Pyridine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (32 mg, 0.13 mmol) in DMF (0.5 mL) is added NaH (95%, 6 mg). The reaction mixture is stirred at room temperature for 30 minutes, and 4-bromo-heptane (137 mg, 0.77 mmol) is added. The mixture is heated at 60° C. for three hours and cooled. To the mixture, water (2 mL) and EtOAc (2 mL) are added. The organic layer is separated, washed with water once and concentrated under reduced pressure. The residue is purified by PTLC (Hexane/EtOAc 4:1) to give the titled compound. 1H NMR: (CDCl3) 8.82 (s, 1H), 7.43 (s, 1H), 7.32 (d, 1H), 7.31 (t, 1H), 7.16 (d, 2H), 6.87 (s, 1H), 6.53 (d, 1H), 4.42 (m, 1H), 2.32-2.40 (m, 4H), 1.86-1.95 (m, 4H), 1.15-1.32 (m, 4H), 1.03 (t, 6H), 0.84 (m, 6H).

後処理

  1. temperatureThe mixture is heated at 60° C. for three hours
  2. temperaturecooled
  3. customThe organic layer is separated
  4. washwashed with water once
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by PTLC (Hexane/EtOAc 4:1)

出典と根拠

ORDレコード
ord-1344f35011bf403c932d17ccffa5d501
出典データセット
uspto-grants-2011_03
特許番号
US07906528B2

関連ノート

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