1,10-Phenanthroline → HCID 68338089、化合物

HRID 2172002

反応式

HRID 2172002 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 68338089HCID 68338089、化合物収率 58%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a2be8fb37944461cb5ee74dbbaeb8db7
出典データセット
uspto-grants-2015_06
特許番号
US09051321B2

関連ノート

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