p-Diiodobenzene → tert-Butyl 5-((4-iodophenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710317

Reaction equation

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

Participants

Reactant 4

HCID 12208p-Diiodobenzene

HCID 123701-Octyne

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

HCID 667262485-Iodo-2-tritylisoindoline

Product 1

HCID 66726604tert-Butyl 5-((4-iodophenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 34%

Procedure

When tert-butyl-5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl-carbamate was substituted for 1-octyne and 1,4 diiodobenzene was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 34% yield, as the pale solid. 1H-NMR (CDCl3) 1.43 (s, 3H); 1.46 (s, 9H); 1.48 (s, 3H); 2.40 (s, 1H); 3.99 (d, 2H, J=11.34 Hz); 4.00 (d, 2H, J=11.37 Hz); 5.18 (broad s, 1H); 7.12 (d, 2H, J=8.28 Hz); 7.61 (d, 2H, J=8.28 Hz).

Sources & evidence

ORD record: ord-2ac38624b5b84d1db10a645c9ce73a18
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Linked notes

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