Methanol → HCID 118060709, compound

HRID 2274817Notes

Reaction equation

HRID 2274817 reaction equation
N1C[CH:3]([CH2:5][N:6]2[CH:10]=[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=4)[NH:13][CH:12]=3)[CH:8]=[N:7]2)C1.S(=O)(=O)(O)O.[OH2:26].[CH3:27][OH:28]>>[F:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([C:9]3[CH:8]=[N:7][N:6]([CH2:5][C:3]([O:28][CH3:27])=[O:26])[CH:10]=3)=[CH:12][NH:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 118059901HCID 118059901, compound

Product 1

HCID 118060709HCID 118060709, compoundYield 31%

Conditions

Temperature
85 °C

Procedure

To a solution of 2-(4-(6-fluoro-1H-indol-3-yl)-1H-pyrazol-1-yl)acetic acid (Example 6; 100 mg; 0.39 mmol) in MeOH (10 mL) was added concentrated sulfuric acid (0.02 mL; 0.39 mmol). The mixture was stirred at 85° C. overnight, cooled to r.t., poured into water, extracted with EtOAc (10 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated, and purified by preparative TLC (petroleum ether/EtOAc=1/1) to afford 33 mg (31%) of the title compound as a white solid.

Workup

  1. temperaturecooled to r.t.
  2. extractionextracted with EtOAc (10 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified by preparative TLC (petroleum ether/EtOAc=1/1)

Sources & evidence

ORD record
ord-0f568855bf6e492d9f45c7153233deb5
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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