o-Iodoanisole → HCID 57527248, compound

HRID 1452743Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:21])[CH3:20])#[CH:11]>>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]1[N:18]([C:19](=[O:21])[CH3:20])[C:13]2[C:12]([CH:10]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

Reactant 2

HCID 68257o-Iodoanisole

HCID 10261360N-(2-ethynylphenyl)acetamide

Product 1

HCID 57527248HCID 57527248, compoundYield 83%

Procedure

The general procedure was used to convert 1-iodo-2-methoxybenzene and N-(2-ethynylphenyl)acetamide to the title product. Purification by flash chromatography gave the analytically pure product as a slightly yellow solid, 83% yield. 1H NMR (300 MHz, CDCl3) δ 8.40-8.36 (m, 1H), 7.57-7.53 (m, 1H), 7.45-7.41 (m, 2H), 7.36-7.22 (m, 2H), 7.09-7.04 (m, 1H) 6.95-6.92 (m, 1H), 6.54 (s, 1H), 3.76 (s, 3H), 2.10 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 171.26, 156.93, 137.29, 136.39, 130.66, 130.55, 129.06, 124.76, 123.43, 123.16, 121.04, 120.21, 116.07, 111.30, 110.65, 55.38, 25.80.

Sources & evidence

ORD record: ord-8ec0a8ed7cab4fa5985850b01b08d500
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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