Cesium fluoride → 2-(((2S,3R)-3-Methyl-1-(5-methyl-2-(pyrimidin-2-yl)benzoyl)piperidin-2-yl)methyl)isoindoline-1,3-dione

HRID 61061

Reaktionsgleichung

I[C:2]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([CH3:12])[C@H:7]1[CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24])=[O:5].C([Sn](CCCC)(CCCC)[C:35]1[N:40]=[CH:39][CH:38]=[CH:37][N:36]=1)CCC.[F-].[Cs+]>CN(C=O)C.[Cu]I.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][C@@H:8]1[CH2:9][CH2:10][CH2:11][N:6]([C:4](=[O:5])[C:3]2[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:2]=2[C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[C@@H:7]1[CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 2-(((2S,3R)-1-(2-iodo-5-methylbenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (0.20 g, 0.40 mmol), 2-(tributylstannyl)pyrimidine (0.15 mL, 0.48 mmol), CsF (121 mg, 0.80 mmol), CuI (15 mg, 0.08 mmol) and Pd(PPh3)4 (46 mg, 0.04 mmol) in DMF (10 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% EtOAc/hexanes) to yield the title compound as a brown oil (0.11 g, 61%). MS (ESI) 455 (M+H).

Aufarbeitung

customwas degassed
customThe solvent was removed in vacuo
customto obtain the crude which
customwas purified by silica gel chromatography (0˜100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-2dc197c40dba492ea83c0cb5f4ac5257
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09440982B2

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