1,10-Phenanthroline → HCID 68338089, 화합물

HRID 82946

반응식

HRID 82946 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>COCCOC.[Cu]I>[O:10]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

참가 물질

6

반응물 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 68338101tert-Butyl (2R)-2-{[(2-bromophenyl)amino]carbonyl}pyrrolidine-1-carboxylate

생성물 1

HCID 68338089HCID 68338089, 화합물수율 58%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
85 °C

실험 절차

In a 25 mL flask, tert-butyl (2R)-2-{[(2-bromophenyl)amino]carbonyl}pyrrolidine-1-carboxylate (194 mg, 0.53 mmol; which may be prepared as described in Step 1) was dissolved in DME (4 mL) under nitrogen at room temperature. CuI (6 mg, 0.03 mmol), Cs2CO3 (261 mg, 0.80 mmol) and 1,10-phenanthroline (26 mg, 0.14 mmol) were added then the reaction mixture was heated at 85° C. for 24 h. The mixture was cooled to room temperature and concentrated to dryness. The residue was dissolved in dichloromethane and filtered on Celite to eliminate the cupper residue. The filtrate was concentrated and the residue purified on preparative TLC (Pentane/EtOAc, 85/15 to 50/50) to give the title compound (88 mg, 58%) as a solid.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane
  4. filtrationfiltered on Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified on preparative TLC (Pentane/EtOAc, 85/15 to 50/50)

출처 및 근거

ORD 기록
ord-66350c97b8a943dca51859ef6d5544af
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846711B2

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