Sulfuric Acid → HCID 67313995, compound

HRID 1011422Notes

Reaction equation

HRID 1011422 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-f023d3fb0a514131992908bedcd7b91d
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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