Methanol → Methyl 3-methyl-1-[(trifluoromethyl)sulfonyl]-1H-indazole-6-carboxylate

HRID 1880393Notes

Reaction equation

HRID 1880393 reaction equation
FC(F)(F)S(O[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:23])=[N:12][N:13]2[S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])=[CH:9][CH:8]=1)(=O)=O.[CH2:26](N(CC)CC)C.[CH3:33][OH:34].[OH2:35]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:23][C:11]1[C:10]2[C:14](=[CH:15][C:7]([C:33]([O:35][CH3:26])=[O:34])=[CH:8][CH:9]=2)[N:13]([S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[N:12]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 22663384HCID 22663384, compound

Product 1

HCID 22663352Methyl 3-methyl-1-[(trifluoromethyl)sulfonyl]-1H-indazole-6-carboxylateYield 69%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-1-[(trifluoromethyl)sulfonyl]-1H-indazol-6-yl trifluoromethanesulfonate (0.61 g, 1.5 mmol) in DMF (6 mL) was flushed with CO for 5 minutes. The solution was treated with palladium acetate (68 mg, 0.30 mmol), 1,1′-bis(diphenylphosphino)ferrocene (167 mg, 0.30 mmol), triethylamine (0.33 g, 0.45 mL, 3.2 mmol) and methanol (4 mL). The mixture was stirred at room temperature under CO (1 atm). The solution was poured into water and extracted with EtOAc (3×). The combined organic extracts were concentrated and purified by Biotage (40S column, 8% EtOAc/heptane) to provide methyl 3-methyl-1-[(trifluoromethyl)sulfonyl]-1H-indazole-6-carboxylate (330 mg, 69%).

Workup

  1. extractionextracted with EtOAc (3×)
  2. concentrationThe combined organic extracts were concentrated
  3. custompurified by Biotage (40S column, 8% EtOAc/heptane)

Sources & evidence

ORD record
ord-120ef0eeb703433da63bed576701cda6
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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