Pyridine → HCID 67196680, compound

HRID 469198Notes

Reaction equation

HRID 469198 reaction equation
N1C=CC=CC=1.S(Cl)([Cl:9])=O.[CH3:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[S:21]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([I:33])=[CH:30][CH:31]=2)[C:26]([C:35]2[C:36]([O:41][CH2:42][CH3:43])=[N:37][CH:38]=[CH:39][CH:40]=2)(O)[C:25]1=[O:44])(=[O:23])=[O:22]>ClCCl>[Cl:9][C:26]1([C:35]2[C:36]([O:41][CH2:42][CH3:43])=[N:37][CH:38]=[CH:39][CH:40]=2)[C:27]2[C:32](=[CH:31][CH:30]=[C:29]([I:33])[CH:28]=2)[N:24]([S:21]([C:14]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:13]=2[O:12][CH3:11])(=[O:23])=[O:22])[C:25]1=[O:44]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 67196875HCID 67196875, compound

Product 1

HCID 67196680HCID 67196680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (40 μl, 0.46 mmol) and thionyl chloride (35 μl, 0.46 mmol) were added successively to an ice-cooled solution of 1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypridin-3-yl)-3-hydroxy-5-iodo-1,3-dihydroindol-2-one (100 mg, 0.15 mmol) in dichloromethane (30 ml). The reaction mixture was allowed to warm to room temperature and stirred for 3 hours. Ice-water was added to the reaction mixture, and the aqueous phase was extracted with dichloromethane. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting crude product (110 mg) was employed without further purification in the next stage.

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product (110 mg) was employed without further purification in the next stage

Sources & evidence

ORD record
ord-386be9136d19450c8a8d570c1523f486
Source dataset
uspto-grants-2014_01
Patent number
US08629148B2

Reaction notes

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