1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 67343427, Verbindung

HRID 451485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451485
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH:3]=1.Br[C:16]1[N:40]=[C:19]2[C:20]([C:25]3[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=3)[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:21][C:22]([CH3:24])=[CH:23][N:18]2[N:17]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[O-]C1C=CC=CC=1.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C(Cl)Cl>[CH3:24][C:22]1[CH:21]=[C:20]([C:25]2[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=2)[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:33])[CH3:34])[C:19]2[N:18]([N:17]=[C:16]([NH:14][CH:11]3[CH2:12][CH2:13][N:8]([C:4]4[CH:3]=[C:2]([CH3:1])[N:7]=[CH:6][N:5]=4)[CH2:9][CH2:10]3)[N:40]=2)[CH:23]=1

Komponenten

8

Edukt 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4445035Phenolate SodiumHCID 166433141-(6-Methylpyrimidin-4-yl)piperidin-4-amineHCID 67342864Tert-butyl 3-(2-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate

Produkt 1

HCID 67343427HCID 67343427, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 1-(6-methylpyrimidin-4-yl)piperidin-4-amine (52.5 mg, 273 μmol), tert-butyl 3-(2-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate (114 mg, 273 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (12.6 mg, 21.9 μmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (11.3 mg, 10.9 μmol) and sodium phenoxide (50.1 mg, 410 μmol) in dioxane (3 mL) was degassed three times and reacted at 140° C. under an atmosphere of nitrogen in a microwave oven for 1 hour. The title compound was obtained a light yellow solid (46 mg, 32%) after column chromatography on silica gel using a gradient from methylenechloride to a mixture of methylenechlorid/methanol 19:1 (v/v) as eluent.

Aufarbeitung

  1. customreacted at 140° C. under an atmosphere of nitrogen in a microwave oven for 1 hour

Quellen und Nachweise

ORD-Eintrag
ord-1af8b2159f8742c8ac88f93872e9df17
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486967B2

Notizen zur Reaktion

Wird geladen…