Sodium Carbonate → 5-(2-aminopyrimidin-4-yl)-2-(2-chloro-5-cyanophenyl)-1H-pyrrole-3-carboxamide

HRID 924682ノート

反応式

HRID 924682 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11](Br)=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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]>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:19]3[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:18]=3[Cl:17])=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27632792-Chloro-5-cyanophenylboronic acidHCID 497882145-(2-aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxamide

生成物 1

HCID 665710105-(2-aminopyrimidin-4-yl)-2-(2-chloro-5-cyanophenyl)-1H-pyrrole-3-carboxamide収率 13%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

5-(2-Aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxamide (prepared according to WO2007/110344, 0.1 g, 0.35 mmol), 2-chloro-5-cyanophenylboronic acid (127 mg, 0.7 mmol), Na2CO3 (111 mg, 1.05 mmol), and PdCl2(dppf) (28 mg, 0.035 mmol) in DME (2.5 mL) and water (1 mL) were heated at 80° C. for 12 h, under argon. After cooling to room temperature, the precipitate was filtered and the filtrate was evaporated under reduced pressure. The crude material was purified by preparative HPLC (Method 1) to afford the title compound (15 mg, 13%).

後処理

  1. filtrationthe precipitate was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude material was purified by preparative HPLC (Method 1)

出典と根拠

ORDレコード
ord-008ae75dd38741b5b8cd37fd04c35427
出典データセット
uspto-grants-2016_03
特許番号
US09283224B2

反応ノート

読み込み中…