Trimethylsilylacetylene → 4-((6-Ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

HRID 40191

반응식

HRID 40191 반응식
F[B-](F)(F)F.[C:6]([PH+](C(C)(C)C)C(C)(C)C)(C)(C)[CH3:7].C[Si](C#C)(C)C.Br[C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([CH2:35][O:36][C:37]3[C:46]4[C:41](=[CH:42][C:43]([O:47][CH3:48])=[CH:44][CH:45]=4)[N:40]=[CH:39][CH:38]=3)=[N:33][N:34]=2)[CH:31]=1>O1CCOCC1.C(N(CC)CC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[C:6]([C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([CH2:35][O:36][C:37]3[C:46]4[C:41](=[CH:42][C:43]([O:47][CH3:48])=[CH:44][CH:45]=4)[N:40]=[CH:39][CH:38]=3)=[N:33][N:34]=2)[CH:31]=1)#[CH:7]

참가 물질

8

반응물 3

HCID 66111TrimethylsilylacetyleneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 576910274-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

생성물 1

HCID 866302634-((6-Ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8471Triethylamine용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

Tri-t-butylphosphonium tetrafluoroborate (0.0377 g, 0.130 mmol), tris(dibenzylideneacetone)dipalladium (0.0594 g, 0.0649 mmol), trimethylsilyl acetylene (1.82 ml, 13.0 mmol), 4-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline (0.500 g, 1.30 mmol) were taken up in dioxane (10 mL) and triethylamine (3 mL). Added CuI. Sealed in a tube and heated at 80° C. for 3 h. Concentrated. Took up in MeOH and added solid potassium carbonate (large excess). Allowed to stir for 30 min. Filtered through a plug of Celite and concentrated. Took up in 10% MeOH in DCM and filtered through a plug of silica gel to afford 4-((6-ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline. MS m/z=331.0 [M+1]+. Calc'd for C19H14N4O2: 330.3.

후처리

  1. customSealed in a tube
  2. concentrationConcentrated
  3. additionadded solid potassium carbonate (large excess)
  4. filtrationFiltered through a plug of Celite
  5. concentrationconcentrated
  6. filtrationfiltered through a plug of silica gel

출처 및 근거

ORD 기록
ord-9ee07d29b49a4cf8a703c00f9149bf69
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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