Methanesulfonyl chloride → 3-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]quinoline

HRID 128947ノート

反応式

HRID 128947 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][CH2:14]O)[CH:2]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[C:30]1([C:36]2[CH2:37][CH2:38][NH:39][CH2:40][CH:41]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1>[C:30]1([C:36]2[CH2:41][CH2:40][N:39]([CH2:14][CH2:13][C:12]#[C:11][C:3]3[CH:2]=[N:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:38][CH:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

7

反応物 5

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 516892Sodium BicarbonateHCID 106317924-(3-Quinolinyl)-3-butyn-1-ol

生成物 1

HCID 99058843-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]quinoline

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

反応条件

温度
0 °C

実験手順

A solution of the alcohol prepared in Step (a) (1.98 g, 0.01 mol), N,N-diisopropylethylamine (3.5 mL, 0.02 mol) and a catalytic amount of 4-dimethylaminopyridine is cooled to 0° C., and methanesulfonyl chloride (0.8 mL, 0.0105 mol) is added dropwise. The solution is stirred at 0° C. for 18 hours, and then concentrated under reduced pressure. The residue is taken up in dimethylformamide (20 mL), and to this solution is added 4-phenyl-1,2,3,6-tetrahydropyridine (2.41 g, 0.015 mol) and sodium bicarbonate (3.4 g, 0.04 mol). The mixture is heated at 40° C. for 5 hours, and the solvent is removed under reduced pressure. The residue is partitioned between 50 mL of ethyl acetate and 50 mL of water. The aqueous layer is extracted with 50 mL of ethyl acetate and the combined organic layers are dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 2% methanol/ 98% dichloromethane) to give the title compound, containing 0.4 mol of water; mp 94.3°-95.8° C.

後処理

  1. concentrationconcentrated under reduced pressure
  2. temperatureThe mixture is heated at 40° C. for 5 hours
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is partitioned between 50 mL of ethyl acetate and 50 mL of water
  5. extractionThe aqueous layer is extracted with 50 mL of ethyl acetate
  6. dry with materialthe combined organic layers are dried (sodium sulfate)
  7. customthe solvent is removed in vacuo
  8. customThe residue is chromatographed (silica gel, 2% methanol/ 98% dichloromethane)

出典と根拠

ORDレコード
ord-5e92b144ce7641c29a6fc6faaedd7915
出典データセット
uspto-grants-1995_11
特許番号
US05466698

反応ノート

読み込み中…