4-Fluorophenylboronic acid → HCID 17888045, compound

HRID 271302Notes

Reaction equation

HRID 271302 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>COCCOC.C([O-])([O-])=O.[Na+].[Na+]>[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

5

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 5813924-Chloro-2-methylpyridine

Product 1

HCID 17888045HCID 17888045, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 4-chloro-2-methylpyridine (10 g, 79 mmol) and (4-fluorophenyl)boronic acid (13.2 g, 94 mmol) in DME (150 ml) and 2M Na2CO3 (94 ml) was degassed for 5 minutes with a stream of nitrogen before adding Pd(PPh3)4 (1.8 g, 2 mol %) and then refluxing overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (30 ml), washed with 4 N NaOH (40 ml) and then with brine (50 ml). The organic layer was then dried over MgSO4, concentrated in vacuo and purified by chromatography on silica gel eluting with a gradient 30-50% ethyl acetate/hexane to afford 9.0 g of the title compound (61%): δH (360 Mz, CDCl3) 2.62 (3H, s), 7.16 (2H, t, J 8.5), 7.27 (1H, d, J 5.0), 7.33 (1H, s), 7.58-7.62 (2H, m), 8.53 (1H, d, J 5.0); m/z (ES+) 188 (MH30 ).

Workup

  1. customwas degassed for 5 minutes with a stream of nitrogen
  2. additionbefore adding Pd(PPh3)4 (1.8 g, 2 mol %)
  3. temperaturerefluxing overnight
  4. additiondiluted with ethyl acetate (30 ml)
  5. washwashed with 4 N NaOH (40 ml)
  6. dry with materialThe organic layer was then dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. custompurified by chromatography on silica gel eluting with a gradient 30-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-24070714631f4a6f886bf1bb21929d78
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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