Phenylacetylene → 5-Chloro-7-fluoro-2-phenyl-1H-indole

HRID 1452737Notes

Reaction equation

HRID 1452737 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([NH2:9])=[C:4]([F:10])[CH:3]=1.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([F:10])[CH:3]=1)[NH:9][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 27736504-Chloro-2-fluoro-6-iodoaniline

Product 1

HCID 251596595-Chloro-7-fluoro-2-phenyl-1H-indoleYield 92%

Procedure

The general procedure was used to convert 4-Chloro-2-fluoro-6-iodo-phenylamine and phenylacetylene 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 12.13 (s, 1H), 7.98-7.95 (d, J=7.72, 2H), 7.51-7.46 (t, J=7.53, 2H), 7.44 (s, 1H), 7.40-7.35 (t, J=7.72, 1H), 7.11-7.07 (d, J=10.92, 1H), 6.96 (s, 1H). 13C NMR (75 MHz, DMSO) δ 150.98, 147.70, 141.53, 133.51, 132.04, 129.73, 129.04, 126.54, 124.59, 124.10, 116.44, 108.27, 100.39. Anal. Calcd. for C14H9ClFN: C, 68.44; H, 3.69; Cl, 14.43; F, 7.73; N, 5.70. Found C, 68.26; H, 3.76; Cl, 14.70; F, 7.5; N, 5.72. m.p.: 153-155° C.

Sources & evidence

ORD record
ord-387f20151256452392008605f4851e53
Source dataset
uspto-grants-2009_01
Patent number
US07473786B1

Reaction notes

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