1-Octyne → tert-Butyl-2,2-dimethyl-5-((4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)prop-1-ynyl)phenyl)ethynyl)-1,3-dioxan-5-ylcarbamate

HRID 710314

Reaktionsgleichung

Reaktionsgleichung von HRID 710314
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[CH:17])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C#CCCCCCC.[F:27][C:28]([F:51])([F:50])[C:29]([C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]([CH2:40][C:41]#[C:42][C:43]2[CH:48]=[CH:47][C:46](I)=[CH:45][CH:44]=2)[CH:32]=1)=[O:30].IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[C:17][C:46]2[CH:47]=[CH:48][C:43]([C:42]#[C:41][CH2:40][N:33]3[C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:31]([C:29](=[O:30])[C:28]([F:27])([F:51])[F:50])=[CH:32]3)=[CH:44][CH:45]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 123701-OctyneHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 667262485-Iodo-2-tritylisoindolineHCID 667264982,2,2-Trifluoro-1-(1-(3-(4-iodophenyl)prop-2-ynyl)-1H-indol-3-yl)ethanone

Produkt 1

HCID 131733934tert-Butyl-2,2-dimethyl-5-((4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)prop-1-ynyl)phenyl)ethynyl)-1,3-dioxan-5-ylcarbamateAusbeute 90 %

Versuchsvorschrift

When tert-butyl-5-ethynyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was substituted for 1-octyne and the product of Step C was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 90% yield, as light yellow paste. 1H-NMR (CDCl3) 1.43 (s, 3H); 1.45 (s, 9H); 1.48 (s, 3H); 3.94-4.13 (m, 4H), 5.18 (s, 2H); 7.34-7.41 (m, 6H); 7.52-7.55 (m, 1H); 8.12 (b, 1H); 8.37-8.43 (m, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-1ea14f8d602c414e9a854268904a7bf0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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