Dimethylformamide → Irsenontrine

HRID 1043971ノート

反応式

HRID 1043971 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([C@H:16]4[CH2:20][CH2:19][O:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[CH3:21][O:22][C:23]1[C:28]([CH3:29])=[C:27](B(O)O)[C:26]([CH3:33])=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:21][O:22][C:23]1[C:28]([CH3:29])=[C:27]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:15]([C@H:16]5[CH2:20][CH2:19][O:18][CH2:17]5)[N:14]=[CH:13][C:7]=4[C:8](=[O:12])[NH:9][C:10]=3[CH:11]=2)[C:26]([CH3:33])=[CH:25][N:24]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 86686333HCID 86686333、化合物HCID 136387814(S)-7-bromo-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one

生成物 1

HCID 136253996Irsenontrine

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

(S)-7-bromo-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one (100 mg), (2-methoxy-3,5-dimethyl-pyridin-4-yl)boronic acid (65 mg) obtained in Preparation Example 29 (4) and cesium carbonate (293 mg) were added to a mixed solution of DMF (5 mL) and water (1 mL) at room temperature. PdCl2(PPh3)2 (10.5 mg) was added to the mixture in a nitrogen gas stream. The mixture was stirred at 80° C. for one hour and at 100° C. for 4.5 hours. After cooling the reaction mixture to room temperature, water (5 mL) was added, and the mixture was extracted with isopropyl acetate. The organic layer was washed with water and brine and then concentrated under reduced pressure. A crude purified product (64.7 mg) was obtained as the title compound. The instrumental data of this compound were identical to those of the (−)-form of Example 25.

後処理

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. extractionthe mixture was extracted with isopropyl acetate
  3. washThe organic layer was washed with water and brine
  4. concentrationconcentrated under reduced pressure
  5. customA crude purified product (64.7 mg)

出典と根拠

ORDレコード
ord-261d236098c04660b56b4640e6b2f56c
出典データセット
uspto-grants-2013_10
特許番号
US08563565B2

反応ノート

読み込み中…