Water → HCID 57479071, compound

HRID 556467Notes

Reaction equation

HRID 556467 reaction equation
Br[C:2]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[C:21]1([NH:27][CH2:28][CH2:29][OH:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)([N:27]([CH2:28][CH2:29][OH:30])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:3](=[O:12])[NH:4]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31235N-(2-Hydroxyethyl)anilineHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 57479071HCID 57479071, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (370 mg, 1 mmol), N-phenylethanolamine (165 mg, 1.2 mmol) and K2CO3 (276 mg, 2 mmol) in DMF (2 mL) was stirred at room temperature for 3 h. The mixture was poured into water (30 mL), extracted with ethyl acetate (10 mL×3). The organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified with chromatography to give 51 mg of rac-6-chloro-3-(3-chloro-benzyl)-3-[(2-hydroxy-ethyl)-phenyl-amino]-1,3-dihydro-indol-2-one as a white solid. MS: [M+H]+=427.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified with chromatography

Sources & evidence

ORD record
ord-3cf3528a1e2e48169a1be256952c2e24
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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