Water → ethyl [4-({2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}amino)-1H-indol-1-yl]acetate

HRID 2389382Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl[CH2:18][CH2:19][N:20]1[CH:25]=[C:24]([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]1=[O:39].O>CCO>[C:27]1([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:24]2[CH:23]=[CH:22][C:21](=[O:39])[N:20]([CH2:19][CH2:18][NH:1][C:2]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:3]=3[CH:4]=[CH:5][N:6]4[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:25]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of ethyl (4-amino-1H-indol-1-yl)acetate (94 mg) in EtOH (7 mL) was added 1-(2-chloroethyl)-5-(diphenylmethyl)-2(1H)-pyridinone (70 mg) at ambient temperature. The reaction mixture was warmed to 50° C. After 24 hours, to the mixture was added water and the resulting mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:EtOAc=5:1) to give ethyl [4-({2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}amino)-1H-indol-1-yl]acetate (45 mg).

Workup

extractionthe resulting mixture was extracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated in vacuo
customThe residue was purified by preparative thin-layer chromatography (chloroform:EtOAc=5:1)

Sources & evidence

ORD record: ord-fea7ee1b709444c2844b8dad67d9095a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273745B2

Reaction notes

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