Sodium Carbonate → HCID 17888045, compound

HRID 552486Notes

Reaction equation

HRID 552486 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.[F-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O.C(OCC)C.C(Cl)(Cl)Cl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=2)=[CH:12][CH:11]=1

Participants

11

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 522689Potassium FluorideHCID 5813924-Chloro-2-methylpyridine

Product 1

HCID 17888045HCID 17888045, compoundYield 133.5%

Reagents, catalysts & solvents 6

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Argon was bubbled for 15 min through a suspension of 1.11 ml (1.276 g, 10.0 mmol) 4-Chloropicoline, 2.798 g (20.0 mmol, 2.0 equiv.) of 4-Fluorophenylboronic acid, and 1.917 g (33.0 mmol, 3.3 equiv.) of KF in 20 ml of Dioxane. Then 155 mg (0.15 mmol, 1.5 mol %)Pd2(dba)3×CHCl3 and 104 ul (93 mg, 0.45 mmol, 4.5 mol %) Tri-tert-butylphosphine were added. The mixture was then stirred for 1 h under argon at 100° C. The reaction was worked up in the usual manner with diethylether, water, and sodium carbonate solution. The combined organic phases were washed with 30 ml of water, dried and concentrated in vaccuo to yield 2.5 g of a light yellow oil which was purified by flash chromatography (heptane/ethyl acetate 1:1) to yield the title compound (1.81 g, 97%) as a white solid, MS (ISP): m/e=188.3 (M+H)+.

Workup

  1. washThe combined organic phases were washed with 30 ml of water
  2. customdried
  3. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-9c43ad370e294a5ca0f4ef565ba987a5
Source dataset
uspto-grants-2011_05
Patent number
US07951824B2

Reaction notes

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