Triethylamine → 3-[3-(2-Methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine

HRID 502796노트

반응식

HRID 502796 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]#[CH:13])[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.[NH2:21][C:22]1[C:27](Br)=[CH:26][C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=1>O1CCCC1.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>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]#[C:13][C:27]2[C:22]([NH2:21])=[N:23][CH:24]=[C:25]([N+:29]([O-:31])=[O:30])[CH:26]=2)[CH:9]=[CH:10][CH:11]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 27344122-Amino-3-bromo-5-nitropyridineHCID 714077821-Ethynyl-3-(2-methoxyethoxy)benzene

생성물 1

HCID 684671423-[3-(2-Methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine수율 74.5%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

3-(2-Methoxy-ethoxy)-phenylacetylene (6.3 g, 36 mmol) was added to a solution of triethylamine (1.92 mL, 14 mmol), 2-amino-3-bromo-5-nitropyridine (4 g, 18 mmol), PdCl2(PPh3)2 (966 mg, 1.38 mmol) and CuI (262 mg, 1.38 mmol) in anhydrous tetrahydrofuran (80 mL) in the dark. The mixture was stirred at room temperature for 48 hours then concentrated in vacuo and resolvated in dichloromethane (150 mL). The organic solution was washed with water (25 mL), dried over MgSO4, filtered and concentrated in vacuo to 20% of its original volume and heptane (20 mL) was then added. The resultant yellow solid was filtered and dried to give 3-[3-(2-methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine (4.2 g, 74% yield).

후처리

  1. concentrationthen concentrated in vacuo
  2. washThe organic solution was washed with water (25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to 20% of its original volume and heptane (20 mL)
  6. additionwas then added
  7. filtrationThe resultant yellow solid was filtered
  8. customdried

출처 및 근거

ORD 기록
ord-ac9c557432594dedb36e832d89609042
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776878B2

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