2-Iodoaniline → HCID 25159658, compound

HRID 1452735Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][CH:4]=1)#[CH:2].I[C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14]>>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:14][C:13]3[C:15]([CH:10]=2)=[CH:16][CH:17]=[CH:18][CH:12]=3)=[CH:5][CH:4]=1)=[CH2:2]

Participants

Reactant 2

HCID 119952-Iodoaniline

HCID 109424411-Ethenyl-4-ethynylbenzene

Product 1

HCID 25159658HCID 25159658, compoundYield 72%

Procedure

The general procedure was used to convert 1-Ethynyl-4-vinyl-benzene and 2-iodoaniline to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 72% yield. 1H NMR (300 MHz, CDCl3) δ 8.31 (s, br, 1H), 7.64-7.61 (d, J=8.29, 3H), 7.49-7.46 (d, J=8.29, 2H), 7.40-7.38 (d, J=8.10, 1H), 7.22-7.16 (dt, J=6.97, 1H), 7.14-7.09 (dt, J=7.91, 1H), 6.84 (s, 1H), 6.78-6.69 (dd, J=10.73, 1H), 5.82-5.76 (dd, J=17.70, 1H), 5.30-5.26 (dd, J=10.73, 1H). Anal. Calcd. for C16H13N: C, 87.64; H, 5.98; N, 6.39.

Sources & evidence

ORD record: ord-92bad07d88994efd953bbe8cf9598db9
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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