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

HRID 61274Notes

Reaction equation

HRID 61274 reaction equation
[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6](I)[C:5]([CH3:12])=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[N:14]1.CN[C@H]1CCCC[C@@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([N:14]2[N:15]=[CH:16][CH:17]=[N:13]2)[C:5]([CH3:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 1177276746-Fluoro-2-iodo-3-methylbenzoic acidHCID 178418936HCID 178418936, compound

Product 1

HCID 1177276806-fluoro-3-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-fluoro-2-iodo-3-methylbenzoic acid (900 mg, 3.21 mmol), 1,2,3-triazole (208 μl, 4.82 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (103 μl, 642 μmol), Cs2CO3 (1.57 g, 4.82 mmol) and CuI (61 mg, 321 μmol) in DMF (5 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The reaction was cooled to rt, diluted with MeOH, and acidified with AcOH to pH 4˜5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (40% EtOAc in hexanes) to yield the title compound. MS (ESI) 222 (M+H).

Workup

  1. customwas degassed
  2. temperatureThe reaction was cooled to rt
  3. additiondiluted with MeOH
  4. customThe solvent was removed in vacuo
  5. customto obtain the crude which
  6. customwas purified by silica gel chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-dd156d9f2d94499a98d8f06742f76bf0
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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