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

5-Bromonicotinonitrile → Tert-butyl 4-[3-(5-cyanopyridin-3-yl)prop-2-ynylidene]piperidine-1-carboxylate

HRID 1895966
ノート
印刷プレビュー

反応式

HRID 1895966 の反応式
[CH:1](=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].Br[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([CH:25]=1)[C:23]#[N:24]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:23]([C:22]1[CH:25]=[C:18]([C:3]#[C:2][CH:1]=[C:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH:19]=[N:20][CH:21]=1)#[N:24]
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

5

反応物 2

HCID 7367935-BromonicotinonitrileHCID 86661548tert-Butyl 4-(prop-2-yn-1-ylidene)piperidine-1-carboxylate

生成物 1

HCID 25183829Tert-butyl 4-[3-(5-cyanopyridin-3-yl)prop-2-ynylidene]piperidine-1-carboxylate収率 100%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 6102075
Dichlorobis(triphenylphosphine)palladium
触媒

反応条件

温度
80 °C

実験手順

A mixture of Compound 2b (0.5 g, 2.26 mmol), 5-bromonicotinonitrile (0.511 g, 2.26 mmol), bis(triphenylphosphine)palladium(II)dichloride (80 mg, 0.05 mmol), CuI (43.1 mg, 0.1 mmol) in anhydrous and degassed triethylamine (12.6 mL) was heated at 80° C. under a nitrogen atmosphere for 2 h in a sealed vessel. The reaction mixture was cooled, filtered on Celite, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 4:96 to 30:70) affording the title product (0.731 g).

後処理

  1. customdegassed triethylamine (12.6 mL)
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered on Celite
  4. additionpoured into water
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. customdried on Na2SO4
  8. customevaporated to dryness in vacuo
  9. customto afford a residue, which
  10. customwas purified by flash chromatography (EtOAc—Petroleum Ether gradient from 4:96 to 30:70)

出典と根拠

ORDレコード
ord-42c85cdf19894ecebce7f923b5165288
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08518916B2

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