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

HRID 924682노트

반응식

HRID 924682 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-008ae75dd38741b5b8cd37fd04c35427
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283224B2

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