Ethyl Acetate → HCID 118162104, compound

HRID 1749400Notes

Reaction equation

HRID 1749400 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O1CCOCC1.O.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 131269094-Chloropyrimidine-5-carbonitrile

Product 1

HCID 118162104HCID 118162104, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloropyrimidine-5-carbonitrile (1.0 equiv.), (4-fluorophenyl)boronic acid (1.2 equiv.), 1,1′-bis(diphenylphosphino ferrocene-palladium(ii)dichloride dichloromethane complex (10 mol %) and potassium carbonate (3.0 equiv.) in dioxane/water 3:1 (0.5 M) was purged with nitrogen for 3 min. The pressure reaction vessel was tightly capped and heated at 100° C. for 5 h. Ethyl acetate and water were added and layers were separated. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give a brown, sticky oil, which was purified by silica gel column chromatography (0-30% ethyl acetate in hexane, 100 g column) to give the title compound (58% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ (ppm) 9.39 (s, 1H), 9.06 (s, 1H), 8.23-8.17 (m, 2H), 7.31-7.27 (m, 2H). MS (ESI) m/z 200.2 [M+1]+.

Workup

  1. customwas purged with nitrogen for 3 min
  2. customThe pressure reaction vessel
  3. customwas tightly capped
  4. customlayers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a brown, sticky oil, which
  9. customwas purified by silica gel column chromatography (0-30% ethyl acetate in hexane, 100 g column)

Sources & evidence

ORD record
ord-b2ab1737f51440c19e8072a980552804
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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