Phenylacetylene → 5,7-dichloro-2-phenyl-1h-indole

HRID 1452736Notes

Reaction equation

HRID 1452736 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4](I)[C:3]=1[NH2:10].[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[Cl:8][C:6]1[CH:5]=[C:4]2[C:3](=[C:2]([Cl:1])[CH:7]=1)[NH:10][C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:18]2

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 75775252,4-dichloro-6-iodoaniline

Product 1

HCID 2192435,7-dichloro-2-phenyl-1h-indoleYield 85%

Procedure

The general procedure was used to convert 2,4-Dichloro-6-iodo-phenylamine and phenylacetylene to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 85% yield. 1H NMR (300 MHz, DMSO) δ 11.82 (s, 1H), 8.01-7.98 (d, J=8.2, 2H), 7.57 (s, 1H), 7.51-7.46 (t, J=7.15, 2H), 7.40-7.36 (t, J=7.15, 1H), 7.26 (d, J=1.88, 1H), 6.95 (d, J=2.07, 1H). 13C NMR (75 MHz, DMSO) δ 141.99, 133.71, 131.98, 131.86, 129.60, 129.10, 126.98, 124.85, 121.56, 119.11, 117.40, 100.90. Anal. Calcd. for C14H9Cl2N: C, 64.15; H, 3.46; Cl, 27.05; N, 5.34. Found C, 64.09; H, 3.37; Cl, 27.05; N, 5.28. m.p.: 135.5-137.5° C.

Sources & evidence

ORD record
ord-63704f4f2af049bd8ea3a71e5c0c8871
Source dataset
uspto-grants-2009_01
Patent number
US07473786B1

Reaction notes

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