3-Bromopyridine → HCID 57803058, compound

HRID 2102704Notes

Reaction equation

HRID 2102704 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18](=[O:24])[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1>O1CCCC1>[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([OH:24])([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 122863-BromopyridineHCID 2413316-Chloroindoline-2,3-dioneHCID 178418339Butyllithium

Product 1

HCID 57803058HCID 57803058, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of n-butyllithium (2.0 M in hexanes, 3.45 mL, 7.5 mmol) (Aldrich) in tetrahydrofuran (3 mL) at −78° C. was added a solution of 3-bromo-pyridine (0.96 g, 8.1 mmol) (Aldrich) in tetrahydrofuran (6 mL) dropwisely. After the addition, the resulting dark solution was stirred for additional 15 minutes. A solution of 6-chloroisatin (0.5 g, 2.76 mmol) (Crescent) in tetrahydrofuran (5 mL) was added dropwisely and the crude was warmed up to room temperature and stirred at room temperature for 3 hours. The reaction was quenched with water. The mixture was extracted with ethyl acetate three times. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography to give rac-6-Chloro-3-hydroxy-3-pyridin-3-yl-1,3-dihydro-indol-2-one as a yellow solid. (Yield 0.27 g, 37%).

Workup

  1. additionAfter the addition
  2. stirringstirred at room temperature for 3 hours
  3. customThe reaction was quenched with water
  4. extractionThe mixture was extracted with ethyl acetate three times
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-d7caa855245c4472ab96959da31b4a39
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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