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

Potassium Acetate → 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one

HRID 577598
ノート
印刷プレビュー

反応式

HRID 577598 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[CH3:16][N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[N:18]1.CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.C([O-])(=O)C.[K+]>CC(O)(CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][N:17]1[C:21]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][NH:8][C:9]3=[O:12])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=2)=[C:20]([CH3:22])[N:19]=[N:18]1
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

7

反応物 4

HCID 517044Potassium AcetateHCID 11371790Bis(adamantan-1-yl)(butyl)phosphaneHCID 152571421,4-Dimethyl-1H-1,2,3-triazoleHCID 825721717-bromo-5-nitroisoquinolin-1(2H)-one

生成物 1

HCID 867238257-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one収率 60%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 64052-Methyl-2-butanol溶媒

反応条件

温度
120 °C

実験手順

A mixture of 7-bromo-5-nitroisoquinolin-1(2H)-one (293b, 4.00 g, 14.9 mmol), 1,4-dimethyl-1H-1,2,3-triazole (2.17 g, 22.3 mmol), palladium acetate (334 mg, 1.49 mmol), CatacXiumA (butyl di-1-adamantylphosphine) (1.10 g, 2.97 mmol), and potassium acetate (7.30 g, 74.3 mmol) in 2-methyl-2-butanol (100 mL) was degassed with nitrogen, and heated at 120° C. in a sealed tube overnight. After cooling down room temperature, the reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic phase was separated, washed with brine (1×300 mL), dried over sodium sulfate, concentrated to dryness, and purified by silica gel chromatography (eluting with a gradient of 0%-10% methanol in ethyl acetate), affording 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-nitroisoquinolin-1(2H)-one (293c, 2.55 g, 60% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 11.95 (br. s., 1H), 8.57 (s, 2H), 7.55 (d, J=5.38 Hz, 1H), 6.98 (d, J=7.34 Hz, 1H), 4.00 (s, 3H), 2.29 (s, 3H). MS: 284 [M−1].

後処理

  1. customwas degassed with nitrogen
  2. temperatureAfter cooling down room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate (300 mL) and water (300 mL)
  4. customThe organic phase was separated
  5. washwashed with brine (1×300 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. custompurified by silica gel chromatography (
  9. washeluting with a gradient of 0%-10% methanol in ethyl acetate),

出典と根拠

ORDレコード
ord-4af0cc07c1024da7ace15f6b0501fcb9
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040515B2

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