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

HRID 1581676Notes

Reaction equation

HRID 1581676 reaction equation
C(Cl)CCl.[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.[CH3:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]1[CH2:25][NH:26][CH3:27].C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([N:26]([CH3:27])[CH2:25][C:17]1[N:16]([CH3:15])[C:24]2[C:19]([CH:18]=1)=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:10]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 69402-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 227220782-Bromo-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]benzamideYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (660 mg, 3.44 mmole) was added to a solution of 2-bromobenzoic acid (693 mg, 3.45 mmole), 1-methyl-2-(methylaminomethyl)indole (600 mg, 3.45 mmole), and HOBt.H2O (466 mg, 3.45 mmole) in DMF at RT. The reaction was stirred overnight, then was concentrated in vacuo. The residue was diluted with 5% NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine and dried over MgSO4. Flash chromatography on silica gel (2% MeOH/CH2Cl2) gave the title compound (750 mg, 63%): MS (ES) m/e 357 (M+H)+.

Workup

  1. customat RT
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with 5% NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-ee8a0ba7b78a4b0da7a549a14e2d8c43
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Reaction notes

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