Water → (1-Methyl-1H-benzoimidazol-2-YL)-[3-(3-phenyl-pyrazin-2-YL)-azetidin-1-YL]-methanone

HRID 1850318ノート

反応式

HRID 1850318 の反応式
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]([C:14]3[N:18]([CH3:19])[C:17]4[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]=3)=[O:13])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:19][N:18]1[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]=[C:14]1[C:12]([N:10]1[CH2:11][CH:8]([C:3]2[C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9]1)=[O:13]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58546825HCID 58546825、化合物

生成物 1

HCID 58546740(1-Methyl-1H-benzoimidazol-2-YL)-[3-(3-phenyl-pyrazin-2-YL)-azetidin-1-YL]-methanone収率 70%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of [3-(3-chloro-pyrazin-2-yl)-azetidin-1-yl]-(1-methyl-1H-benzoimidazol-2-yl)-methanone (100 mg, 0.30 mmol) in dioxane (10 mL) was added phenylboronic acid (87 mg, 0.71 mmol), Na2CO3 (152 mg, 1.4 mmol) and H2O (2 mL). The reaction mixture was degassed with N2 and then PdCl2(dppf) (35 mg, 0.05 mmol) was added. The reaction mixture was stirred at 80° C. for 12 h. The reaction mixture was left to reach RT and filtered through a pad of CELITE® and the filter cake was washed with CH2Cl2 (20 mL×3). The combined filtrates were evaporated in vacuo and the residue was purified by column chromatography to give the desired compound (60 mg, 0.17 mmol, yield 70%)

後処理

  1. customThe reaction mixture was degassed with N2
  2. waitThe reaction mixture was left
  3. customto reach RT
  4. filtrationfiltered through a pad of CELITE®
  5. washthe filter cake was washed with CH2Cl2 (20 mL×3)
  6. customThe combined filtrates were evaporated in vacuo
  7. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-d88ad0087c894acb9ea3ccff4c228d80
出典データセット
uspto-grants-2015_02
特許番号
US08957073B2

反応ノート

読み込み中…