Water → 4-(2-Fluoropyridin-3-YL)tetrahydro-2H-pyran-4-carbaldehyde

HRID 1880093Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[O:8])[CH2:3][CH2:2]1.Br[C:10]1[C:11]([F:16])=[N:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:16][C:11]1[C:10]([C:4]2([CH:7]=[O:8])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a sealed tube was added tetrahydro-2H-pyran-4-carbaldehyde (0.25 g, 2.190 mmol), 3-bromo-2-fluoropyridine (0.321 g, 1.825 mmol), palladium(ii) acetate (0.016 g, 0.073 mmol), cesium carbonate (0.714 g, 2.190 mmol), water (1.644 μL, 0.091 mmol), BINAP (0.068 g, 0.110 mmol) in Dioxane (7.30 mL). The resulting mixture was heated to 100° C. overnight. More catalyst and ligand (palladium(ii) acetate (0.016 g, 0.073 mmol), binap (0.068 g, 0.110 mmol)) were added and the resulting mixture was heated to 113° C. until the starting material was completely consumed. Aqueous work up followed by DCM extraction. Purification by Biotage (0-100% MeOH/DCM) & prep-plate TLC (5% MeOH/DCM) produced product which was advanced to the next step.

Workup

temperaturethe resulting mixture was heated to 113° C. until the starting material
customwas completely consumed
extractionAqueous work up followed by DCM extraction
customPurification by Biotage (0-100% MeOH/DCM)
customproduced product which

Sources & evidence

ORD record: ord-e439a6c834c74dce87f31df40b9e8303
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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