Triethylamine → 2-Bromo-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]benzamide

HRID 1581675Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[CH2:21][NH:22][CH3:23].CCN(CC)CC>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:22]([CH3:23])[CH2:21][C:13]1[N:12]([CH3:11])[C:20]2[C:15]([CH:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-bromobenzoyl chloride (1.85 g, 8.45 mmole) in CH2Cl2 (10 mL) was added dropwise to a solution of 1-methyl-2-(methylaminomethyl)indole (1.47 g, 8.45 mmole) and Et3N (3.6 mL, 25.8 mmole) in CH2Cl2 (50 mL) at 0° C. The reaction was stirred at 0° C. for 15 min, then was allowed to warm to RT. After 2 hr, the mixture was concentrated in vacuo, and the residue was diluted with H2O. The mixture was extracted with Et2O, and the combined Et2O layers were dried (MgSO4) and concentrated in vacuo. The oily residue was triturated with Et2O/petroleum ether to afford the title compound (2.6 g, 87%) as a white solid: MS (ES) m/e 357 (M+H)+.

Workup

temperatureto warm to RT
waitAfter 2 hr
concentrationthe mixture was concentrated in vacuo
additionthe residue was diluted with H2O
extractionThe mixture was extracted with Et2O
dry with materialthe combined Et2O layers were dried (MgSO4)
concentrationconcentrated in vacuo
customThe oily residue was triturated with Et2O/petroleum ether

Sources & evidence

ORD record: ord-9ddeb3f3465d40cf8fa45805d876cc1f
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730684B1

Reaction notes

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