Triethylamine → HCID 58100104、化合物

HRID 1696848ノート

反応式

HRID 1696848 の反応式
C(N(CC)CC)C.I[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[I:15].[CH2:16]([N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])[CH2:17][C:18]#[CH:19]>O1CCCC1.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[I:15][C:10]1[CH:11]=[CH:12][C:13]([C:19]#[C:18][CH2:17][CH2:16][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])=[CH:14][CH:9]=1

参加物

7

反応物 3

HCID 8471Triethylamine2 回HCID 119941,2-DiiodobenzeneHCID 11171619N-(3-Butynyl)phthalimide

生成物 1

HCID 58100104HCID 58100104、化合物収率 51.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution containing triethylamine (250 mL), copper (I) iodide (1.72 g, 9.09 mmol) and diiodobenzene (56) (20.00 g, 60.60 mmol) dissolved in anhydrous tetrahydrofuran (250 mL) was stirred at room temperature. The reaction flask was evacuated and then purged with nitrogen three times. The solution was treated with bis(triphenylphosphine) palladium(II) dichloride (4.20 g, 6.06 mmol) and continued to stir at room temperature for 30 min. A solution containing triethylamine (250 mL) and 2-but-3-ynylisoindole-1,3-dione (12.06 g, 60.06 mmol) dissolved in anhydrous tetrahydrofuran (250 mL) was added dropwise through an addition funnel over 12 hours. The reaction was allowed to stir at room temperature for 48 h. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the desired product 57 (12.5 g, 51%) as a brown solid: 1H NMR (500 MHz, CD2Cl2) δ 7.85 (dd, 2H), 7.74 (dd, 2H), 7.60 (d, 2H), 7.04 (d, 2H), 3.92 (t, 2H), 2.79 (t, 2H); m/z (ESI) 402 [C18H12INO2+H]+.

後処理

  1. customThe reaction flask was evacuated
  2. custompurged with nitrogen three times
  3. stirringto stir at room temperature for 30 min
  4. additionwas added dropwise through an addition funnel over 12 hours
  5. stirringto stir at room temperature for 48 h
  6. filtrationThe solution was filtered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe resulting residue was purified by column chromatography
  9. washeluting with 0-100% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-b0c58ab292234cbf8dbd3cd41ac330ef
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

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