Allyltributylstannane → HCID 178446223, Verbindung

HRID 1947269Notizen

Reaktionsgleichung

[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21](I)[CH:20]=4)[CH2:14][CH2:13]3)[N:11]([CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])[C:10](=[O:31])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:32]([Sn](CCCC)(CCCC)CCCC)[CH:33]=[CH2:34]>CN(C=O)C.CCOC(C)=O.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>[CH2:34]([C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][N:15]1[CH2:16][CH2:17][C:12]2([N:11]([CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])[C:10](=[O:31])[N:9]=[C:8]2[NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:13][CH2:14]1)[CH:33]=[CH2:32]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 4-(cyclohexylamino)-8-(3-iodobenzyl)-1-pent-4-en-1-yl-1,3,8-triazaspiro[4.5]dec-3-en-2-one (920 mg, 1.72 mmol, intermediate I.1.d.1) and trans-bis(triphenylphosphine)palladium(II) chloride (121 mg, 0.17 mmol) in degassed DMF (11.5 mL) was added allyl tri-n-butyltin (0.61 mL, 1.98 mmol) in one portion. The reaction mixture was stirred at 90° C., sealed, for 16 h, diluted with EtOAc, washed with aqueous LiCl twice, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (90 g silica gel, EtOAc) to give the desired product. LRMS (M+1)=449.

Aufarbeitung

customsealed, for 16 h
washwashed with aqueous LiCl twice
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography (90 g silica gel, EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-05a948d0015948789343865cc23e7a88
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08399473B2

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