Trifluoroacetic acid → HCID 67996724, compound

HRID 1467314Notes

Reaction equation

HRID 1467314 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl.Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 679849753-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid

Product 1

HCID 67996724HCID 67996724, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

The synthetic intermediate from Step 1 (392 mg, 0.791 mmol), dichloromethane (2 ml), and trifluoroacetic acid (2 ml) were combined in an open vial. Triethylsilane (1.011 ml, 6.33 mmol) was then added, and the resulting mixture was stirred at a temperature of 23° C. for 50 minutes. The reaction mixture was then diluted with dichloromethane, and 2N HCl was added drop-wise until the pH of the mixture was between 4 and 5. This resulting precipitate was collected via filtration and rinsed with water, methanol and dichloromethane to afford 3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxylic acid (220 mg, 0.674 mmol, 85% yield) as a green solid. The crude product was progressed to the next step without purification.

Workup

  1. additionwas added drop-wise until the pH of the mixture
  2. filtrationThis resulting precipitate was collected via filtration
  3. washrinsed with water, methanol and dichloromethane

Sources & evidence

ORD record
ord-ddc6a999266e45efb22620ed51efadd2
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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