Pyridine → 3,5-Dichloro-3-(2-methoxypyridin-3-yl)-1,3-dihydroindol-2-one

HRID 2040426Notes

Reaction equation

N1C=CC=CC=1.S(Cl)(Cl)=O.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[C:15]2([C:23]1[C:24]([O:29][CH3:30])=[N:25][CH:26]=[CH:27][CH:28]=1)O.[Cl-:31].[NH4+]>ClCCl>[Cl:31][C:15]1([C:23]2[C:24]([O:29][CH3:30])=[N:25][CH:26]=[CH:27][CH:28]=2)[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([Cl:11])[CH:13]=2)[NH:17][C:16]1=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Pyridine (0.33 ml) and thionyl chloride (0.30 ml) were added successively to an ice-cold solution of the intermediate from Step A (1.1 g, 3.44 mmol) in dichloromethane (10 ml). The reaction mixture was stirred at 0° C. for 1 h and then saturated ammonium chloride solution was added. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude intermediate was rapidly employed without further purification in the next step.

Workup

dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude intermediate was rapidly employed without further purification in the next step

Sources & evidence

ORD record: ord-5553c7d2ceee4b35bf1a3b2bdaed94a6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580842B2

Reaction notes

Loading…