Cesium carbonate → 5-fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1193065Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-fluoro-2-iodo-benzoic acid (3.86 g, 14.65 mmol), 2H-[1,2,3]triazole (2.5 g, 36.2 mmol), Cs2CO3 (8.62 g, 24.5 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (0.4 mL), CuI (244 mg) and DMF (13 mL) were added to a microwave ready vessel and heated to 100° C. for 10 min. The mixture was cooled, diluted with water, and extracted with EtOAc. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAc/DCM) gave the product as a white powder, (2.14 g, 71%). 1H NMR (400 MHz, CD3OD): 7.91 (s, 2H), 7.76 (dd, J=8.9, 4.8 Hz, 1H), 7.59 (dd, J=8.5, 2.9 Hz, 1H), 7.49-7.42 (m, 1H).

Workup

temperatureThe mixture was cooled
extractionextracted with EtOAc
extractionextracted with EtOAc
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customThe residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAc/DCM)

Sources & evidence

ORD record: ord-7bea81cc7fa445aa9304dfbb2701d89b
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680275B2

Reaction notes

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