1,2-Dichloroethane → HCID 9930024, compound

HRID 1581690Notes

Reaction equation

HRID 1581690 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1.[CH3:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[CH2:29][NH:30][CH3:31].C1C=CC2N(O)N=NC=2C=1.O.CCN(CC)CC.C(Cl)CCl>CN(C=O)C.C(Cl)Cl>[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:30]([CH3:31])[CH2:29][C:21]2[N:20]([CH3:19])[C:28]3[C:23]([CH:22]=2)=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:9])=[C:5]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 69554926HCID 69554926, compound

Product 1

HCID 9930024HCID 9930024, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To 4-amino-2-phenoxybenzoic acid hydrochloride (1.0 g, 3.4 mmole) in 1:1 DMF/CH2Cl2 (75 mL) was added 1-methyl-2-(methylaminomethyl)indole (0.61 g, 3.5 mmole), HOBt.H2O (0.47 g, 3.5 mmole), Et3N (1.0 mL, 7.1 mmole), then EDC (0.67 g, 3.5 mmole). The reaction was stirred at RT for 16 hr then was concentrated under vacuum. The residue was taken up in EtOAc (200 mL) and-the solution was washed with water, dried (Na2SO4), and concentrated. Flash chromatography on silica gel (2% MeOH/CHCl3, then rechromatography using 70% EtOAc/hexanes) gave the title compound (0.62 g, 42%) as a white solid: MS (ES) m/e 386.2 (M+H)+.

Workup

  1. concentrationthen was concentrated under vacuum
  2. wash-the solution was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa527a056951470d9d09cc4d24dc60cf
Source dataset
uspto-grants-2004_05
Patent number
US06730684B1

Reaction notes

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