Triethylamine → HCID 58100104, 화합물

HRID 1696848노트

반응식

HRID 1696848 반응식
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

참가 물질

7

반응물 3

HCID 8471Triethylamine2회HCID 119941,2-DiiodobenzeneHCID 11171619N-(3-Butynyl)phthalimide

생성물 1

HCID 58100104HCID 58100104, 화합물수율 51.9%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-b0c58ab292234cbf8dbd3cd41ac330ef
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163758B2

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