Sulfuric Acid → HCID 67313995, compound

HRID 1254154Notes

Reaction equation

HRID 1254154 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.O1CCCCC1[O:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[C:41](=O)[O:40][CH2:39]2.OS(O)(=O)=O.[OH-].[Na+]>O1CCCC1>[OH:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[C:41](=[C:3]1[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][C:2]1=[O:10])[O:40][CH2:39]2

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 220614825-{3-[(Oxan-2-yl)oxy]propyl}-2-benzofuran-1(3H)-oneHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 67313995HCID 67313995, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (193 mg (1.44 mmol) in anhydrous tetrahydrofuran (10 ml) under N2 was added 1.0M LiHMDS/THF solution (2.9 ml, 2.9 mmol). The mixture was stirred at room temperature for 10 minutes, then 5-[3-(tetrahydro-pyran-2-yloxy)-propyl]-3H-isobenzofuran-1-one (200 mg, 0.72 mmol) was added. The mixture was stirred at room temperature for 2.5 hours and poured into 1M H2SO4 solution (20 ml). The mixture was heated at 55° C. for 15 minutes, cooled to room temperature and poured into an ice water (200 ml). The mixture was basified to pH 9 with NaOH solution and stirred overnight. The solid was filtered, washed with water and dried under vacuum to give 3-[5-(3-hydroxy-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as a brown solid (20 mg, 9%).

Workup

  1. stirringThe mixture was stirred at room temperature for 2.5 hours
  2. temperatureThe mixture was heated at 55° C. for 15 minutes
  3. temperaturecooled to room temperature
  4. stirringstirred overnight
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5fc0da96aaef436584524648de0d316e
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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