Sodium Carbonate → HCID 89649569, compound

HRID 2207648Notes

Reaction equation

HRID 2207648 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.[CH2:10]([O:12][C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17](B(O)O)[CH:18]=1)[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:10]([O:12][C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=2)[CH:18]=1)[CH3:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 162174685-Ethoxy-2-fluorophenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 89649569HCID 89649569, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-chloropyridine-2-carbonitrile (4.1 g, 29.56 mmol) and (5-ethoxy-2-fluoro-phenyl)boronic acid (5982.6 mg, 32.52 mmol) in monoglyme (150 mL) was treated with sodium carbonate (29.56 mL, 59.13 mmol) and then PdCl2(PPh3)2 (1037.5 mg, 1.48 mmol) and the mixture was refluxed under argon. After 2 hrs the DME was evaporated and ethyl acetate (200 ml) and water were added and the product was extracted into ethyl acetate (3 times). The extracts were dried (Na2SO4) and concentrated. Chromatography on silica gel (0-50% ethyl acetate in isohexane, using a SNAP340 cartidge on a Biotage SP4) gave 4-(5-ethoxy-2-fluoro-phenyl)pyridine-2-carbonitrile (D111) (6.12 g) as an off white solid;

Workup

  1. customAfter 2 hrs the DME was evaporated
  2. additionethyl acetate (200 ml) and water were added
  3. extractionthe product was extracted into ethyl acetate (3 times)
  4. dry with materialThe extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-749eaa0c2d4a49e1ba4371702f789292
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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