Methanol → HCID 59593308, compound

HRID 1952049Notes

Reaction equation

HRID 1952049 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[C:10]([O:14][C:15](=[O:34])[N:16]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:17]1[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[C:19](F)[N:18]=1)([CH3:13])([CH3:12])[CH3:11].[OH-:35].[K+].O.[CH3:38]O>>[C:10]([O:14][C:15](=[O:34])[N:16]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([OH:24])[C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)=[C:19]([O:35][CH3:38])[N:18]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 59593274HCID 59593274, compound

Product 1

HCID 59593308HCID 59593308, compound

Procedure

To 1H-Pyrrolo[2,3-b]pyridine (1, 90.0 mg, 0.76 mmol) in methanol (30.0 mL) were added (4-chloro-benzyl)-(6-fluoro-5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (65, 300.0 mg, 0.82 mmol) and potassium hydroxide (720.0 mg, 12.83 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature for 2 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the compound (68, 60 mg, 15.9%). MS (ESI) [M+H+]+=495.3.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane
  7. customto give the compound (68, 60 mg, 15.9%)

Sources & evidence

ORD record
ord-f90a02be075d4be3a330eaf659fb5f66
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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