Sodium Chloride → HCID 21194412, compound

HRID 565064Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[C:3]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Cl.[Cl-].[Na+]>CN(C)C=O>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[O:11][CH2:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)[CH:4]=[C:3]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2.00 g (8.57 mmol) of ethyl 1,4-dimethyl-7-hydroxy-2-indolecarboxylate, 4.74 g (34.3 mmol) of potassium carbonate, 1.55 g (9.43 mmol) of 2-picolyl chloride hydrochloride and 40 ml of dimethylformamide was stirred at 50° C. for 2 hours. The reaction mixture was poured into 5% sodium chloride aqueous solution. The mixture was extracted with ethyl acetate. After washing with 5% sodium hydrogencarbonate aqueous solution, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography to give 2.54 g of ethyl 1,4-dimethyl-7-[(pyridin-2-yl)methoxy]-2-indolecarboxylate.

Workup

extractionThe mixture was extracted with ethyl acetate
washAfter washing with 5% sodium hydrogencarbonate aqueous solution
dry with materialthe extract was dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-950d67587fa94eb692c741fcf79390af
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169107A

Reaction notes

Loading…