3-Methylbenzoic acid → 2-{3-[(3-methylbenzoyl)amino]phenyl}-1H-indole-1-carboxamide

HRID 530427Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:17]([NH2:19])=[O:18])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=1.[C:20]1([CH3:29])[CH:25]=[CH:24][CH:23]=[C:22]([C:26](O)=[O:27])[CH:21]=1.Cl.CN(C)CCCN=C=NCC>ClCCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:29][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[C:26]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:17]([NH2:19])=[O:18])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=1)=[O:27]

Participants

Conditions

Temperature: 60 °C

Procedure

To the solution of 2-(3-aminophenyl)-1H-indole-1-carboxamide (50.2 mg, 0.2 mmol, 1 eq) and m-toluic acid (27.5 mg, 1 eq) in anhydrous DCE (2 mL) was added 4-(dimethylamino)pyridine (4.9 mg, 0.2 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (46.1 mg, 1.2 eq). After the reaction was stirred at 60° C. for 1 hour, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper clear solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (EtOAc-Hex 1:10 to 1:1) to give 2-{3-[(3-methylbenzoyl)amino]phenyl}-1H-indole-1-carboxamide as a clear oil which turned into a white foam in vacuo in amount of 34 mg.

Workup

washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine
dry with materiallastly dried with anhydrous sodium sulfate
customThe upper clear solution was decanted
concentrationconcentrated

Sources & evidence

ORD record: ord-a0ce305bd6b743008968cef17637374b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353093B2

Reaction notes

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