Triethylamine → HCID 59599679、化合物

HRID 2266646ノート

反応式

HRID 2266646 の反応式
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH2:4][CH2:3][CH2:2][NH:1]2)=[CH:6][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 939807-Quinolinol, 1,2,3,4-tetrahydro-

生成物 1

HCID 59599679HCID 59599679、化合物収率 7%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.15 g (1.01 mmol) 1,2,3,4-tetrahydro-quinolin-7-ol in 10 ml dichloromethane were added 0.19 g (1.56 mmol) phenylboronic acid, 0.27 g (1.49 mmol) copper(II) acetate, a spatula end of 4 Å molecular sieves and 0.64 ml (5.03 mmol) triethylamine. The reaction mixture was stirred at room temperature for 72 hours and then filtered through celite, washing with dichloromethane. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 15 mg (7%) of the title compound as a light yellow oil. MS (ISP): 226.3 ([M+H]+).

後処理

  1. filtrationfiltered through celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

出典と根拠

ORDレコード
ord-ce204272998546009674e090224a06ef
出典データセット
uspto-grants-2010_12
特許番号
US07858652B2

反応ノート

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