Potassium Phosphate, Tribasic → US8975415, RP53b

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Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[O:16][CH2:15][C:11]1([CH2:14][O:13][CH2:12]1)[C:5]12[CH2:9][O:8][C:7]([NH2:10])=[N:6]1.[C:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[N:27][CH:28]=1)#[C:21][CH3:22].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C1(/C=C/C(=O)/C=C/C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:20]([C:23]1[CH:24]=[C:25]([C:2]2[CH:3]=[C:4]3[C:17](=[CH:18][CH:19]=2)[O:16][CH2:15][C:11]2([CH2:14][O:13][CH2:12]2)[C:5]23[CH2:9][O:8][C:7]([NH2:10])=[N:6]2)[CH:26]=[N:27][CH:28]=1)#[C:21][CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

The mixture of 6′-bromodispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (650 mg, 2.00 mmol), [5-(prop-1-yn-1-yl)pyridin-3-yl]boronic acid (644 mg, 4.00 mmol), (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one-palladium (3:2) (92 mg, 0.10 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (164 mg, 0.400 mmol), and K3PO4 (1.70 g, 8.00 mmol) in DMF (13 mL) was stirred for 16 hours at 110° C. under argon atmosphere. The precipitate formed was removed by filtration with celite and washed with CHCl3. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5) to give 6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (310 mg).

Aufarbeitung

customThe precipitate formed
customwas removed by filtration with celite
washwashed with CHCl3
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5)

Quellen und Nachweise

ORD-Eintrag: ord-c699905624ce45ff8e923dc63880b88b
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08975415B2

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