3-Fluorophenol → HCID 67958741, compound

HRID 72438

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][C:16]1[CH:17]=[N:18][C:19]([N:26]2[CH2:29][CH:28](OS(C)(=O)=O)[CH2:27]2)=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22]>C(#N)C>[Cl:15][C:16]1[CH:17]=[N:18][C:19]([N:26]2[CH2:29][CH:28]([O:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[CH2:27]2)=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 3-Fluorophenol (0.005 ml, 0.056 mmole) in acetonitrile (1 ml), potassium carbonate (10 mg, 0.0728 mmol) were added followed by the addition of methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate (D63) (20 mg, 0.062 mmol). The reaction mixture was heated at 150° C. under microwave irradiation for 10 min (2 cycle of 5 min each) then at 180° C. for 5 min. After solvent evaporation the obtained residue was purified by SPE-Si (10 g) eluting with mixture cyclohexane/ethyl acetate from 95/5 to 90/10. Collected fractions, after solvent evaporation, afforded the title compound D77 (10 mg)

Workup

customAfter solvent evaporation the obtained residue
customwas purified by SPE-Si (10 g)
washeluting with mixture cyclohexane/ethyl acetate from 95/5 to 90/10
customCollected fractions, after solvent evaporation

Sources & evidence

ORD record: ord-87ce8322c9764f05854d307a112e4a3b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Linked notes

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