3-Methylbut-1-yne → 2-Chloro-5-(3-methylbut-1-ynyl)pyridin-4-amine

HRID 43268

반응식

HRID 43268 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][N:3]=1.[CH3:10][CH:11]([CH3:14])[C:12]#[CH:13]>CCN(CC)CC.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.[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([C:13]#[C:12][CH:11]([CH3:14])[CH3:10])=[CH:4][N:3]=1

참가 물질

6

반응물 2

HCID 690193-Methylbut-1-yneHCID 454803662-Chloro-5-iodopyridin-4-amine2회

생성물 1

HCID 580250642-Chloro-5-(3-methylbut-1-ynyl)pyridin-4-amine

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

To a solution of 2-chloro-5-iodopyridin-4-amine (Compound 11, 2.55 g, 10.0 mmol) in Et3N (35 ml) was added Pd(PPh3)2Cl2 (70 mg, 0.10 mmol), CuI (19 mg, 0.10 mmol), and 3-methyl-1-butyne (1.2 ml, 12 mmol). The reaction was stirred at room temperature for 20 h and was quenched with H2O, extracted with EtOAc (Δ2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as an off-white solid.

후처리

  1. customwas quenched with H2O
  2. extractionextracted with EtOAc (Δ2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-c536abf1d78f45489380ea426fc5482d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536339B2

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