Sodium hydride → [6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine

HRID 985486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985486
[H-].[Na+].[CH:3]([Si:6]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[SH:7])([CH3:5])[CH3:4].[H][H].I[C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=1)[O:20][CH2:21][CH2:22][C:23]1[N:28]=[C:27]([CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=1>C1COCC1.C1(C)C=CC=CC=1.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>[CH3:12][CH:11]([Si:6]([CH:3]([CH3:5])[CH3:4])([S:7][C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][CH:33]=1)[O:20][CH2:21][CH2:22][C:23]1[N:28]=[C:27]([CH2:29][NH2:30])[CH:26]=[CH:25][CH:24]=1)[CH:8]([CH3:10])[CH3:9])[CH3:13]

Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 22507076HCID 22507076, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22507077[6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (128 mg, 5.1 mmol) in THF (30 ml) was added triisopropylsilanethiol (1.1 ml, 5.1 mmol) dropwise. After the evolution of hydrogen ceased, a solution of {6-[2-(3-Iodophenoxy)ethyl](2-pyridyl) }methylamine (1.2 g, 3.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (390 mg, 0.3 mmol) in toluene (30 ml) was added. After refluxing for 16 h under argon, the reaction mixture was cooled to room temperature and evaporated under vacuum. The residue was dissolved in ethyl acetate and washed with 1N NaOH and brine. The organic layer was dried with sodium sulfate, filtered, and evaporated. The crude product was chomatrographed over silica gel to yield 1.34 g (95%) of [6-(2-{3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenoxy}ethyl)(2-pyridyl)]methylamine. NMR 1H Cl3CD δ: 7.38 (dd, 1H, J=7.2, 8.0 Hz), 7.04 (m, 3H), 6.77 (m, 1H), 6.52 (d, 1H, J=8.0 Hz), 6.25 (d, 1H, J=4.0 Hz), 4.29 (t, 2H, J=6.8 Hz), 3.06 (t, 2H, J=6.8 Hz), 2.90 (d, 3H, J=8Hz), 1.85 (m, 3H), 1.09 (m, 2H).

Aufarbeitung

  1. temperatureAfter refluxing for 16 h under argon
  2. customevaporated under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH and brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-67852ab832a540cea70b7882f6b9f223
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872730B2

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