Methanol → HCID 68901453, compound

HRID 655261Notes

Reaction equation

HRID 655261 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([CH2:16][C:17]([OH:19])=[O:18])=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.S(=O)(=O)(O)O.[CH3:25]O>>[CH3:25][O:18][C:17](=[O:19])[CH2:16][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:8]=2)[NH:13][CH:14]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 68900355HCID 68900355, compound

Product 1

HCID 68901453HCID 68901453, compoundYield 70%

Procedure

[5-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid (200 mg, 0.78 mmol) was suspended in Methanol (4 mL). Next, sulfuric acid (125 uL) was added and the solution was heated to reflux for 2 hours. The solution was concentrated under vacuum and the crude material was dissolved in dichloromethane, transferred to a separatory funnel and washed with sat. NaHCO3 (aq). The organic layer was dried over Na2SO4 and concentrated down. The crude product was purified by flash chromatography (0-10% Methanol/dichloromethane gradient) to afford the title compound (148 mg, 70% yield). MS m/z=271 [M+H+]+

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe solution was concentrated under vacuum
  4. dissolutionthe crude material was dissolved in dichloromethane
  5. customtransferred to a separatory funnel
  6. washwashed with sat. NaHCO3 (aq)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated down
  9. customThe crude product was purified by flash chromatography (0-10% Methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-42d3540b08ab4e6f9b51bfac62a3d755
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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