Triethylamine → HCID 67428809, compound

HRID 1662593Notes

Reaction equation

HRID 1662593 reaction equation
Cl[C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]1=[O:12].FC(F)(F)C(O)=O.[OH:28][C@H:29]1[CH2:33][NH:32][C@H:31]([C:34]([O:36][CH3:37])=[O:35])[CH2:30]1.CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[Cl:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](=[O:12])[C:2]2([N:32]1[CH2:33][C@H:29]([OH:28])[CH2:30][C@H:31]1[C:34]([O:36][CH3:37])=[O:35])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 219059133,5-Dichloro-3-(2-methoxyphenyl)indolin-2-oneHCID 86625683HCID 86625683, compound

Product 1

HCID 67428809HCID 67428809, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2.28 g of 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one, which is the compound described in Preparation 1.1 of Brochure No. WO01/55130, and the compound obtained in Step 4-1 (8.15 mmol) in CHCl3 (23 ml) was added dropwise 4.49 g of Et3N over 2 minutes under ice cooling, then, the reaction mixture was stirred at room temperature for 13 hours. An aqueous solution of 5% K2CO3 was added to the reaction solution, and the resulting mixture was stirred for 15 minutes. liquid separation was performed, and the aqueous layer was extracted with CHCl3 extraction. The combined organic layer was washed with saturated brine, then, dried over MgSO4, the drying agent was separated by filtration, then, the solution was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc) to obtain 2.37 g of a diastereoisomer mixture of the title compound (colorless amorphous).

Workup

  1. customdescribed in Preparation 1.1 of Brochure No
  2. stirringthe resulting mixture was stirred for 15 minutes
  3. customliquid separation
  4. extractionthe aqueous layer was extracted with CHCl3 extraction
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over MgSO4
  7. customthe drying agent was separated by filtration
  8. concentrationthe solution was concentrated under reduced pressure
  9. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc)

Sources & evidence

ORD record
ord-28918c91071249dc97755b51780d796a
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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