Phenylacetylene → 5-bromo-2-phenyl-1H-indole

HRID 1452738Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4](I)[CH:3]=1.[C:10]1([C:16]#[CH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:17]2

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 8239344-Bromo-2-iodoaniline

Product 1

HCID 8389235-bromo-2-phenyl-1H-indoleYield 60%

Procedure

The general procedure was used to convert 4-bromo-2-iodobenzenamine and phenylacetylene to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 60% yield. 1H NMR (300 MHz, DMSO) δ 11.77 (s, 1H), 7.88-7.85 (d, J=7.4, 2H), 7.72 (s, 1H), 7.50-7.45 (t, J=7.5, 2H), 7.39-7.35 (m, 2H), 7.23-7.20 (dd, J=8.5, 1.8, 1H), 6.89 (s, 1H). 13C NMR (75 MHz, DMSO) δ 139.06, 135.69, 131.54, 130.41, 128.88, 127.78, 125.09, 123.89, 122.04, 113.15, 111.78, 98.16. Anal. Calcd. for C14H10BrN: C, 61.79; H, 3.70; Br, 29.36; N, 5.15. Found C, 61.60; H, 3.74; N, 5.02.

Sources & evidence

ORD record: ord-98d1a48ef21945b3944bb32818e49de6
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473786B1

Reaction notes

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