Triethylamine → 5-Phenylethynyl-pyridin-2-ylamine

HRID 40537

反応式

HRID 40537 の反応式
[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

参加物

8

反応物 3

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

生成物 1

HCID 468541905-Phenylethynyl-pyridin-2-ylamine収率 62%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-9ef69a63f7664327a076ce403c75816c
出典データセット
uspto-grants-2013_09
特許番号
US08530472B2

関連ノート

読み込み中…