Hydrochloric Acid → 1,3-Dihydro-3-(1(3H)-isobenzofuranylidene)-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 1254153Notes

Reaction equation

HRID 1254153 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[C:26]1([C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][O:28]1)=O.Cl.C([O-])(O)=O.[Na+]>CN(C)C=O.O>[C:26]1(=[C:3]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[NH:1][C:2]2=[O:10])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][O:28]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 3163671,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-oneHCID 516892Sodium BicarbonateHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 673143861,3-Dihydro-3-(1(3H)-isobenzofuranylidene)-2H-pyrrolo[3,2-b]pyridin-2-oneYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one (50 mg, 0.37 mmol) in anhydrous N,N-dimethylformamide (5.0 ml) was added 1.0M LiHMDS/THF solution (0.74 ml, 0.74 mmol) under N2. After the mixture was stirred at room temperature for 10 minutes, phthalide was added (40 mg, 0.30 mmol), and then it was continuously stirred at room temperature for 4 hours. The mixture was poured into 2M HCl (4.0 ml), heated at 50° C. for 20 minutes and then poured into water (100 ml). After cooled to room temperature, the mixture was basified to pH 9 with saturated NaHCO3 solution, and was stirred at room temperature overnight. The resulting solid was filtered, washed with water, dried under vacuum and triturated with chloroform to give 3-(3H-isobenzofuran-1-ylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one as a yellow solid (12 mg, 16%).

Workup

  1. stirringit was continuously stirred at room temperature for 4 hours
  2. temperatureheated at 50° C. for 20 minutes
  3. temperatureAfter cooled to room temperature
  4. stirringwas stirred at room temperature overnight
  5. filtrationThe resulting solid was filtered
  6. washwashed with water
  7. customdried under vacuum
  8. customtriturated with chloroform

Sources & evidence

ORD record
ord-707e0ab750c64f889877bdb650cde649
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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