Cesium carbonate → benzyl (1S,5S)-6-(5-cyano-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

HRID 1642188

反応式

HRID 1642188 の反応式
[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.[C:18]([C:20]1[CH:21]=[N:22][CH:23]=[C:24](Br)[CH:25]=1)#[N:19].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([C:20]1[CH:25]=[C:24]([N:6]2[CH2:7][C@@H:1]3[C@H:5]2[CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2]3)[CH:23]=[N:22][CH:21]=1)#[N:19]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 7367935-BromonicotinonitrileHCID 23635906benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

生成物 1

HCID 23635910benzyl (1S,5S)-6-(5-cyano-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate収率 47%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

The product of Example 52D (0.800 g, 3.40 mmol) in toluene (34 mL) was treated with 3-cyano-5-bromopyridine (0.690 g, 3.8 mmol), Pd2(dba)3 (0.0.64 g, 0.10 mmol), BINAP (0.086 g, 0.010 mmol) and Cs2CO3 (0.221 g, 6.80 mmol) and the reaction was heated at 80° C. for 12 hours. The mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 5% MeOH/CH2Cl2) to provide the title compound as a yellow oil (47%, 0.530 g). MS (DCI/NH3) m/z 335 (M+H)+.

後処理

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by chromatography (SiO2, 5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-c8107979e2604bc6bdf67687523e3c42
出典データセット
uspto-grants-2012_02
特許番号
US08119635B2

関連ノート

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