1,10-Phenanthroline → HCID 57399776, 화합물

HRID 553050

반응식

HRID 553050 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 57399776HCID 57399776, 화합물수율 63%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-d7b3f6a35ebe4305b45c46fa11f232cf
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951791B2

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