Cesium carbonate → 2-Fluoro-3-methyl-6-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1747217Notes

Reaction equation

HRID 1747217 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[F:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[C:13](I)[C:9]=1[C:10]([OH:12])=[O:11].[NH:19]1[CH:23]=[CH:22][N:21]=[N:20]1>CN(C=O)C>[F:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]([N:20]2[N:21]=[CH:22][CH:23]=[N:19]2)[C:9]=1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 161248372-Fluoro-6-iodo-3-methylbenzoic acidHCID 178418936HCID 178418936, compound

Product 1

HCID 679825682-Fluoro-3-methyl-6-(2H-1,2,3-triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared in analogy to the procedure described in WO2008/069997. Cs2CO3 (6.98 g, 21.4 mmol) was added portionwise to a RT solution of 2-fluoro-6-iodo-3-methyl-benzoic acid (3.0 g, 10.7 mmol) in DMF (15 mL) under argon followed by 1H-1,2,3-triazole (1.24 mL, 21.4 mmol) and Cu(I)I (103 mg, 0.536 mmol) and the resulting blue suspension was stirred at 80° C. overnight. The reaction mixture was quenched with 2M aq. HCl and filtered through a celite plug before being extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by prep. HPLC (method E) to give the title compound as a pale yellow solid. LC-MS B: tR=0.55 min; [M+H]+=222.01.

Workup

  1. customThe reaction mixture was quenched with 2M aq. HCl
  2. filtrationfiltered through a celite plug
  3. extractionbefore being extracted with DCM (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give the crude product that

Sources & evidence

ORD record
ord-d29d645152d044eeacad0ef52ff9bbd7
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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