ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium Carbonate → N-(3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)phenyl)acrylamide

HRID 1500825
ノート
印刷プレビュー

反応式

HRID 1500825 の反応式
C([NH:5]C1C=C(B(O)O)C=CC=1)(=O)C=C.C([O-])([O-])=O.[Na+].[Na+].[CH3:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=3)C=2)[NH:24]N=1>C1(C)C=CC=CC=1.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]>[N:5]1[C:28]([C:31]2[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=2)=[CH:27][N:26]=[C:25]2[NH:24][CH:21]=[CH:22][C:30]=12
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 103213313-Acrylamidophenylboronic acidHCID 178460022HCID 178460022、化合物

生成物 1

HCID 86300986N-(3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)phenyl)acrylamide

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒
HCID 1140
Toluene
溶媒

反応条件

温度
90 °C

実験手順

A solution of 21 (100 mg, 0.507 mmol) and 2 (84 mg, 0.507 mmol) in toluene and ethanol (4:1 mL) was added Na2CO3 (111.01 mg, 1.014 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (20.7 mg, 0.025 mmol) was added to the reaction. The reaction was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90° C. under sealed condition overnight, allowed to cool to RT, and diluted with chloroform. The organic layer was filtered through Celite and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in 40% ethyl acetate in hexane as an off-white solid 22. MS-ES+264.8; 1H NMR (400 MHz, DMSO-D6) 22: 9.99 (bs, 1H), 9.40 (bs, 1H), 7.25 (bs, 1H), 7.08 (m, 1H), 7.00 (d, 1H), 6.42 (m, 2H), 6.21 (m, 1H), 5.71 (m, 1H).

後処理

  1. customThe reaction was degassed
  2. custompurged with nitrogen for 10 min
  3. customThe reaction was degassed
  4. custompurged with nitrogen for another 10 min
  5. customunder sealed condition overnight
  6. temperatureto cool to RT
  7. additiondiluted with chloroform
  8. filtrationThe organic layer was filtered through Celite
  9. concentrationconcentrated
  10. customto get the crude, which
  11. customwas purified through flash chromatography
  12. washThe compound was eluted in 40% ethyl acetate in hexane as an off-white solid 22

出典と根拠

ORDレコード
ord-5d1289de9dd344bf8b0d1ebea005a164
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206188B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート