Sodium Carbonate → HCID 59226524, compound

HRID 1523512Notes

Reaction equation

Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[F:10][C:11]1[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[F:8][C:7]1[C:2]([C:12]2[CH:13]=[C:14]([F:18])[CH:15]=[C:16]([F:17])[C:11]=2[F:10])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-bromo-3-fluoro-6-methylpyridine (1.0 equiv.) in dioxane (0.2 M) was added 2,3,5-trifluorophenylboronic acid and Pd(dppf)Cl2-DCM (0.1 equiv.). Aqueous sodium carbonate (2M solution, 2.0 equiv.) was added and the reaction was heated in the microwave at 120° C. for 15 min. The solution was partitioned between ethyl acetate and sat. NaHCO3, the organic phase was washed with brine, dried with magnesium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:3) to give 3-fluoro-6-methyl-2-(2,3,5-trifluorophenyl)pyridine in 87% yield. LC/MS=242.1 (M+H), Rt=0.98 min.

Workup

customThe solution was partitioned between ethyl acetate and sat. NaHCO3
washthe organic phase was washed with brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude material was purified via silica gel column chromatography
washeluting with ethyl acetate and hexanes (1:3)

Sources & evidence

ORD record: ord-0d0124d2a2714729ae10a431b81a9874
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079889B2

Reaction notes

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