2-Iodoaniline → 2-(4-methylphenyl)-1H-indole

HRID 1452734Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1)#[CH:2].I[C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13]>>[C:6]1([CH3:9])[CH:7]=[CH:8][C:3]([C:1]2[NH:13][C:12]3[C:14]([CH:2]=2)=[CH:15][CH:16]=[CH:17][CH:11]=3)=[CH:4][CH:5]=1

Participants

Reactant 2

HCID 119952-Iodoaniline

HCID 13018p-Ethynyltoluene

Product 1

HCID 2925992-(4-methylphenyl)-1H-indoleYield 74%

Procedure

The general procedure was used to convert 1-Ethynyl-4-methyl-benzene and 2-iodoaniline to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 74% yield. 1H NMR (300 MHz, DMSO) δ 11.47 (s, 1H), 7.74 (d, J=7.72, 2H), 7.50 (d, J=7.72, 2H), 7.38 (d, J=7.91, 1H), 7.25 (d, J=7.72, 2H), 7.11-7.06 (t, J=7.91, 1H), 7.01-6.96 (t, J=7.35, 1H), 6.83 (s, 1H), 2.34 (s, 3H). 13C NMR (75 MHz, DMSO) δ 138.63, 137.85, 137.60, 130.31, 129.55, 125.77, 122.17, 120.72, 120.14, 112.04, 98.89, 21.65. Anal. Calcd. for C15H13N: C, 86.92; H, 6.32; N, 6.67. Found C, 86.69; H, 6.24; N, 6.76. m.p.: 213-215° C.

Sources & evidence

ORD record: ord-c76ea08b8a5543f6aae78a2617a5b3d3
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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