(3-Methoxy-1-propynyl)tributylstannane → 2-(3-Methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

HRID 922055노트

반응식

HRID 922055 반응식
[CH3:1][O:2][C:3]([C:5]1[C:6](Cl)=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4].C([Sn](CCCC)(CCCC)[C:24]#[C:25][CH2:26][O:27][CH3:28])CCC>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>[CH3:1][O:2][C:3]([C:5]1[C:6]([C:24]#[C:25][CH2:26][O:27][CH3:28])=[N:7][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:9][C:10]=1[CH3:11])=[O:4]

참가 물질

5

반응물 2

HCID 10872067(3-Methoxy-1-propynyl)tributylstannaneHCID 866643312-Chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

생성물 1

HCID 866643322-(3-Methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester수율 63.1%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a solution of 700 mg (2.6 mmol) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester and 1.39 g (3.9 mmol) tributyl(3-methoxyprop-1-ynyl)stannane in dioxane (10 ml) was added 273 mg (0.39 mmol) PdCl2(PPh3)2. Then the reaction solution was heated at 100° C. for 16 h. After cooling to RT the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (5% KF-silica, hexane/EtOAc 19:1) provided 500 mg (1.64 mmol, 63%) 2-(3-methoxyprop-1-ynyl)-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

후처리

  1. temperatureAfter cooling to RT the mixture
  2. filtrationwas filtered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by CC (5% KF-silica, hexane/EtOAc 19:1)

출처 및 근거

ORD 기록
ord-d0e3f87a73614e2284a6ca500ff8af16
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278103B2

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