Hexane → 5-(3,5-Dimethylphenylamino)indole

HRID 1354972Notes

Reaction equation

HRID 1354972 reaction equation
C1(S(O[C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=2)(=O)=O)C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[CH:23]2.CCCCCC>C(OCC)(=O)C>[CH3:17][C:15]1[CH:16]=[C:11]([NH:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][CH:24]=[CH:23]3)[CH:12]=[C:13]([CH3:18])[CH:14]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 788675-AminoindoleHCID 112424723,5-Dimethylphenyl benzenesulfonate

Product 1

HCID 211061305-(3,5-Dimethylphenylamino)indoleYield 74.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the general procedure, 3,5-dimethylphenyl benzenesulfonate (131 mg, 0.5 mmol) was coupled with 5-aminoindole (100 mg, 0.75 mmol) with the reaction time of 4 h. Chromatography on silica gel column with 6:1 hexane:ethyl acetate gave 88 mg (74%) of 5-(3,5-dimethylphenylamino)indole as a pale brown solid; and 16 mg (14%) of 1-(3,5-dimethylphenyl)-5-aminoindole as a white solid.

Sources & evidence

ORD record
ord-993fc1d938d44de283a57d06f200c992
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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