Sodium Carbonate → 5'-(3,5-Dimethylisoxazol-4-yl)spiro[[1,3]dioxolane-2,3'-indolin]-2'-one

HRID 1052953

Reaktionsgleichung

[CH3:1][C:2]1[C:6](B(O)O)=[C:5]([CH3:10])[O:4][N:3]=1.Br[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]12[O:25][CH2:24][CH2:23][O:22]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[CH3:1][C:2]1[C:6]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[C:15]23[O:25][CH2:24][CH2:23][O:22]2)=[C:5]([CH3:10])[O:4][N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 3,5-dimethylisoxazol-4-ylboronic acid (159 g, 1.13 mol), dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) (23.6 g, 29 mmol), 5′-bromospiro[[1,3]dioxolane-2,3′-indolin]-2′-one (236 g, 0.87 mol) and Na2CO3 (184 g, 1.7 mol) in dioxane/H2O (1200 mL/300 mL) was heated to 110° C. for 12 h. The mixture was filtered through a pad of celite and concentrated in vacuo. The crude product was dissolved in CH2Cl2 (2 L), then hexane 2 L was added and the mixture was filtered again, the organic phase was concentrated in vacuo to give target product (150 g, 60%). 1H NMR (400 MHz, DMSO-d6): δH 10.56 (s, 1H), 7.31-7.33 (m, 2H), 6.93 (d, J=8.0 Hz, 1H), 4.27-4.35 (m, 4H), 2.35 (s, 3H), 2.18 (s, 3H). MS (ESI) m/e [M+1]+ 287.

Aufarbeitung

filtrationThe mixture was filtered through a pad of celite
concentrationconcentrated in vacuo
dissolutionThe crude product was dissolved in CH2Cl2 (2 L)
additionhexane 2 L was added
filtrationthe mixture was filtered again
concentrationthe organic phase was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-72e7937554db43e59b6e0687f4539861
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09393232B2

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