4-Iodotoluene → HCID 25159789, compound

HRID 1452741Notes

Reaction equation

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

Participants

Reactant 2

HCID 122074-Iodotoluene

HCID 10261360N-(2-ethynylphenyl)acetamide

Product 1

HCID 25159789HCID 25159789, compoundYield 57%

Procedure

The general procedure was used to convert 1-iodo-4-methylbenzene and N-(2-ethynylphenyl)acetamide to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 57% yield. 1H NMR (300 MHz, DMSO) δ 8.24-8.22 (d, J=8.2, 1H), 7.61-7.59 (d, J=6.3, 1H), 7.43-7.40 (d, J=8.0, 2H), 7.36-7.24 (m, 4H), 6.71 (s, 1H), 2.37 (s, 3H), 2.07 (s, 3H). 13C NMR (75 MHz, DMSO) δ 171.94, 140.70, 138.95, 137.81, 131.53, 130.12, 129.67, 129.64, 125.44, 124.26, 121.31, 116.24, 111.41, 28.41, 21.70. Anal. Calcd. for C17H15NO: C, 81.90; H, 6.06; N, 5.62. Found C, 81.66; H, 6.02; N, 5.62. m.p.: 67-69° C.

Sources & evidence

ORD record: ord-e3b3c13489b84c2bbc9db5ec0b217a47
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

Loading…