Formamide → 3-(5-Chloro-2-dimethylaminomethyl-1H-indol-4-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione

HRID 1161889Notes

Reaction equation

C(O[C:4](=O)[CH2:5][C:6]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[C:9]([CH2:16][N:17]([CH3:19])[CH3:18])[NH:10]2)C.[CH:21]([NH2:23])=[O:22].[CH3:24][O-:25].[Na+].[CH3:27][N:28]([CH:30]=O)C>CO>[Cl:15][C:14]1[C:6]([C:5]2[C:21](=[O:22])[NH:23][C:24](=[O:25])[C:4]=2[C:9]2[C:8]3[C:27](=[CH:4][CH:5]=[CH:6][CH:7]=3)[NH:28][CH:30]=2)=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH2:16][N:17]([CH3:18])[CH3:19])=[CH:8]2

Participants

Conditions

Temperature: 105 °C

Procedure

(5-Chloro-2-dimethylaminomethyl-1H-indol-4-yl)-acetic acid ethyl ester (187 mg, 0.63 mmol) and formamide (84 microL, 2.12 mmol) are dissolved under an atmosphere of argon in dry DMF (1.5 ml). The solution is heated to 105° C., and NaOMe (118 microL of a 5.4 M solution in MeOH, 0.63 mmol) is added dropwise during 10 minutes. After 1 hour at 105° C., TLC analysis indicates complete consumption of the starting material. The reaction mixture is cooled to RT, diluted with water, and the pH value is adjusted to 7 by addition of aqueous 1 M NaHSO4. The mixture is concentrated, and the solid residue is purified by FCC (CH2Cl2/EtOH/aq NH3 70:27:3) to afford the title compound. ES-MS: 266.7 [M+H]+.

Workup

customconsumption of the starting material
temperatureThe reaction mixture is cooled to RT
additiondiluted with water
additionthe pH value is adjusted to 7 by addition of aqueous 1 M NaHSO4
concentrationThe mixture is concentrated
customthe solid residue is purified by FCC (CH2Cl2/EtOH/aq NH3 70:27:3)

Sources & evidence

ORD record: ord-e09a71fea8f14455988246adb64bfc1e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820672B2

Reaction notes

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