1-Bromo-4-iodobenzene → Tert-butyl-5-((4-bromophenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

반응식

[C:1]([C:3]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)#[CH:2].C#CCCCCCC.[Br:27][C:28]1[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=1.IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[C:14]([O:13][C:12](=[O:18])[NH:11][C:3]1([C:1]#[C:2][C:31]2[CH:32]=[CH:33][C:28]([Br:27])=[CH:29][CH:30]=2)[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)([CH3:17])([CH3:16])[CH3:15]

참가 물질

반응물 4

HCID 115221-Bromo-4-iodobenzene

HCID 123701-Octyne

HCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate

HCID 667262485-Iodo-2-tritylisoindoline

생성물 1

HCID 131733944Tert-butyl-5-((4-bromophenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate수율 63%

실험 절차

When tert-butyl 5-ethynyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was substituted for 1-octyne and 4-bromo-iodobenzene was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 63% yield, as a pale paste, which solidified on standing. 1H-NMR (CDCl3) 1.43 (s, 2H); 1.46 (s, 9H); 1.48 (s, 3H); 4.00 (d, 2H, J=11.35 Hz); 4.08 (d, 2H, J=11.41 Hz); 5.19 (s, 1H); 7.26 (d, 2H, J=6.74 Hz); 7.41 (d, 2H, J=6.67 Hz).