Sodium Carbonate → [3-(2-Chloro-4-methanesulfonyl-benzyloxy)-2-ethoxy-phenyl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 1261174Notes

Reaction equation

HRID 1261174 reaction equation
[Cl:1][C:2]1[CH:39]=[C:38]([S:40]([CH3:43])(=[O:42])=[O:41])[CH:37]=[CH:36][C:3]=1[CH2:4][O:5][C:6]1[C:7]([O:33][CH2:34][CH3:35])=[C:8]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([Si](C(C)C)(C(C)C)C(C)C)[CH:15]=2)=[O:13])[CH:9]=[CH:10][CH:11]=1.[OH-].[K+].[F-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CO>[Cl:1][C:2]1[CH:39]=[C:38]([S:40]([CH3:43])(=[O:41])=[O:42])[CH:37]=[CH:36][C:3]=1[CH2:4][O:5][C:6]1[C:7]([O:33][CH2:34][CH3:35])=[C:8]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:13])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 522689Potassium FluorideHCID 58087362[3-(2-Chloro-4-methanesulfonyl-benzyloxy)-2-ethoxy-phenyl]-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Product 1

HCID 58086239[3-(2-Chloro-4-methanesulfonyl-benzyloxy)-2-ethoxy-phenyl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-ethoxy-3-hydroxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (666, 84 mg, 0.054 mmol) in methanol (10 mL) was added potassium hydroxide (6 N solution) until pH of the solution turned to over 10. Potassium fluoride (30 mg, 0.5 mmol) was then added to the reaction mixture and the mixture was stirred at room temperature for 6 hours. The reaction mixture was then poured into saturated sodium carbonate and was extracted with ethyl acetate. The organic layer was collected and washed with brine, dried over magnesium sulfate. After removal of the solvent, the residue was purified by preparative HPLC to provide as a white solid (P-2094, 5 mg, 19%). MS (ESI) [M+H+]+=485.17.

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer was collected
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was purified by preparative HPLC
  7. customto provide as a white solid (P-2094, 5 mg, 19%)

Sources & evidence

ORD record
ord-9da436cd8054400d8806febfd3600b24
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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