홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

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

HRID 1895966
노트
인쇄 미리보기

반응식

HRID 1895966 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

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

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-42c85cdf19894ecebce7f923b5165288
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08518916B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트