Cesium carbonate → 1-Methyl-5-(pyridin-4-yl)-3,4-dihydroisoquinoline

HRID 926242노트

반응식

HRID 926242 반응식
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[CH3:12].[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:7]1[C:8]2[C:3](=[C:2]([C:16]3[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][N:6]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 867113155-Iodo-1-methyl-3,4-dihydroisoquinoline

생성물 1

HCID 867113191-Methyl-5-(pyridin-4-yl)-3,4-dihydroisoquinoline수율 73.8%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5-iodo-1-methyl-3,4-dihydroisoquinoline (3.0 g, 11.1 mmol), pyridin-4-ylboronic acid (2.04 g, 16.6 mmol), Pd(PPh3)2Cl2 (3.88 g, 5.53 mmol) and Cs2CO3 (10.8 g, 33.2 mmol) in 1,4-dioxane (45 mL) was heated to reflux for 24 h. The mixture was allowed to cool to RT, and then filtered. The filter cake was washed with AcOEt, and the filtrate was then concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1) to afford the title compound (1.82 g) as a grey solid. UPLC-MS: MS 223.0 (M+H+); UPLC rt 0.38 min.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. filtrationfiltered
  4. washThe filter cake was washed with AcOEt
  5. concentrationthe filtrate was then concentrated in vacuo
  6. customThe crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1)

출처 및 근거

ORD 기록
ord-8f7e61e86c7647dfaabf4cbc67099387
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284331B2

반응 노트

불러오는 중…