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Triethylamine → 2-(6-{3-[(1-Methylpiperidin-4-yloxy)-pyridin-2-ylmethyl]phenyl}hex-5-ynyl)isoindole-1,3-dione

HRID 593381
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 593381
I[C:2]1[CH:3]=[C:4]([CH:8]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:23]([N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])[CH2:24][CH2:25][CH2:26][C:27]#[CH:28].C(N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.CN1CCCC1=O>[CH3:22][N:19]1[CH2:20][CH2:21][CH:16]([O:15][CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:4]2[CH:3]=[C:2]([C:28]#[C:27][CH2:26][CH2:25][CH2:24][CH2:23][N:29]3[C:33](=[O:34])[C:32]4[C:31](=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:30]3=[O:39])[CH:7]=[CH:6][CH:5]=2)[CH2:17][CH2:18]1
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Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 3346053N-(5-Hexynyl)phthalimideHCID 726947252-[(3-Iodophenyl)(1-methylpiperidin-4-yloxy)methyl]pyridine

Produkt 1

HCID 867038712-(6-{3-[(1-Methylpiperidin-4-yloxy)-pyridin-2-ylmethyl]phenyl}hex-5-ynyl)isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A screw-cap tube is charged with 2-[(3-iodophenyl)(1-methylpiperidin-4-yloxy)methyl]pyridine (105 mg, example 37), tetrakis(triphenylphosphine)palladium (52 mg), copper(I) iodide (26 mg), N-5-hexynylphthalimide (186 mg), triethylamine (400 μL) and 1-methyl-2-pyrrolidinone (4 mL). The tube is evacuated, filled with argon and sealed. After stirring at 90° C. for 14 h, the mixture is diluted with water and the aqueous phase is extracted with ethyl acetate. The pooled organic extracts are washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 95/5/0.5) to give 2-(6-{3-[(1-methylpiperidin-4-yloxy)-pyridin-2-ylmethyl]phenyl}hex-5-ynyl)isoindole-1,3-dione as an brown oil.

Aufarbeitung

  1. customThe tube is evacuated
  2. additionfilled with argon
  3. customsealed
  4. additionthe mixture is diluted with water
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. washThe pooled organic extracts are washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 95/5/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-13f67e5db34b494785dc05860f9d275d
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242959B2

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