Triethylamine → 5-Phenylethynyl-pyridin-2-ylamine

HRID 40537

반응식

HRID 40537 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:9]1([C:15]#[C:16][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 885792-Pyridinamine, 5-iodo-

생성물 1

HCID 468541905-Phenylethynyl-pyridin-2-ylamine수율 62%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

Bis-(triphenylphosphine)-palladium(II)dichloride (480 mg, 0.68 mmol, 0.05 equiv.) was dissolved in 50 ml THF. (3 g, 13.6 mmol) 2-Amino-5-iodopyridine and phenylacetylene (2.79 g, 27.3 mmol, 2.0 equiv.) were added at room temperature. Triethylamine (5.58 ml, 40.9 mmol, 3 equiv.), triphenylphosphine (111 mg, 0.41 mmol, 0.03 equiv.) and copper(I)iodide (70 mg, 0.41 mmol, 0.03 equiv.) were added and the mixture was stirred for 2 hours at 65° C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and three times with ethyl acetate. The organic layers were combined, dried over sodium sulfate and evaporated to dryness. The crude product was suspended in dichloromethane, filtered and the solid evaporated to dryness. The desired 5-phenylethynyl-pyridin-2-ylamine (1.6 g, 62% yield) was obtained as a light yellow solid, MS: m/e=195.3 (M+H+).

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with saturated NaHCO3 solution and three times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. filtrationfiltered
  6. customthe solid evaporated to dryness

출처 및 근거

ORD 기록
ord-9ef69a63f7664327a076ce403c75816c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530472B2

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