Phenylacetylene → 2-Phenylindole

HRID 1452733Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]>>[C:1]1([C:7]2[NH:12][C:11]3[C:13]([CH:8]=2)=[CH:14][CH:15]=[CH:16][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 119952-Iodoaniline

Product 1

HCID 136982-Phenylindole

Procedure

The general procedure was used to convert phenylacetylene and 2-iodoaniline to the title product. Purification by flash chromatography gave the analytically pure product as a white solid (92% yield). 1H NMR (300 MHz, DMSO) δ 11.54 (s, 1H), 7.86-7.84 (d, J=7.15, 2H), 7.53-7.50 (d, J=7.72, 1H), 7.45-7.40 (t, J=7.72, 3H), 7.30-7.25 (t, J=7.34, 1H), 7.01-6.96 (t, J=6.97, 1H), 6.87 (s, 1H). 13C NMR (75 MHz, DMSO) δ 138.48, 138.01, 133.09, 132.43, 132.30, 129.76, 129.25, 128.24, 125.84, 122.44, 120.93, 120.24, 112.18, 99.55. Anal. Calcd. for C14H11N: C, 87.01; H, 5.74; N, 7.25. Found C, 86.87; H, 5.72; N, 6.99. m.p.: 183-184° C.

Sources & evidence

ORD record: ord-19bf64a4fd094bf98fbdf741107cab99
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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