1,10-Phenanthroline → HCID 57399776、化合物

HRID 553050

反応式

HRID 553050 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12](Br)=[CH:13][C:8]=3[S:7](=[O:16])(=[O:15])[C:6]=2[CH:17]=1.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C@H:20]([OH:26])[CH2:19]2.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[O:15]=[S:7]1(=[O:16])[C:6]2[CH:17]=[CH:2][CH:3]=[CH:4][C:5]=2[C:9]2[CH:10]=[CH:11][C:12]([O:26][C@H:20]3[CH:21]4[CH2:24][CH2:25][N:18]([CH2:23][CH2:22]4)[CH2:19]3)=[CH:13][C:8]1=2

参加物

7

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 7364113-Quinuclidinol, (+)-HCID 40718983,7-DibroModibenzothiophene dioxide

生成物 1

HCID 57399776HCID 57399776、化合物収率 63%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A mixture of 3,7-dibromodibenzothiophene-5,5-dioxide (0.60 g, 1.75 mmol; see J. Med. Chem. 1978, 21, 1084), (S)-(−)-quinuclidin-3-ol (280 mg, 2.2 mmol; Acros), copper (I) iodide (33 mg, 0.17 mmol; Aldrich), 1,10-phenanthroline (63 mg, 0.35 mol; Aldrich) and powdered cesium carbonate (0.86 g, 2.64 mmol; Aldrich) in toluene (2 mL) was heated to 110° C. with vigorous stirring for 30 h. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth, rinsing with ethyl acetate and dichloromethane, and the residue purified by flash chromatography (80 g silica gel, 1:10:89 NH4OH-MeOH—CH2Cl2) to afford the title compound (0.37 g, 1.08 mmol; 63% yield): MS (DCI/NH3): m/z 342 (M+1)+.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through diatomaceous earth
  3. washrinsing with ethyl acetate and dichloromethane
  4. customthe residue purified by flash chromatography (80 g silica gel, 1:10:89 NH4OH-MeOH—CH2Cl2)

出典と根拠

ORDレコード
ord-d7b3f6a35ebe4305b45c46fa11f232cf
出典データセット
uspto-grants-2011_05
特許番号
US07951791B2

関連ノート

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