Dichloromethane → HCID 66643904, compound

HRID 1187050Notes

Reaction equation

HRID 1187050 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([O:10][CH3:11])[CH:3]=1.ClCCl.[CH2:15](N(CC)CC)[CH3:16]>C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl.CCO>[CH:15]([C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([O:10][CH3:11])[CH:3]=1)=[CH2:16]

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 547588416-Chloro-4-methoxypyridine-3-carbonitrile

Product 1

HCID 66643904HCID 66643904, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A 20 mL microwave tube was charged with 6-chloro-4-methoxypyridine-3-carbonitrile (200.0 mg, 1.2 mmol), bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (97.0 mg, 0.12 mmol), potassium vinyl trifluoroborate (318.0 mg, 2.37 mmol), and triethylamine (0.33 mL, 2.37 mmol), and EtOH (6 mL). The microwave tube was evacuated and filled with nitrogen (two times) and heated to 140° C. After 1 h, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The extracts were concentrated and chromatographed over a column of SiO2 (0-30% EtOAc/hexanes as eluent). Evaporation of the solvent yielded the title compound. 1H NMR (500 MHz, DMSO-d6), δ 8.65 (s, 1H), 6.89 (s, 1H), 6.83 (dd, J=10.7 Hz, 1H), 6.42 (d, J=7.3 Hz, 1H), 5.70 (d, J=10.6 Hz, 1H) 4.05 (s, 3H);

Workup

  1. customThe microwave tube was evacuated
  2. additionfilled with nitrogen (two times)
  3. additionthe reaction mixture was diluted with water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe extracts were concentrated
  8. customchromatographed over a column of SiO2 (0-30% EtOAc/hexanes as eluent)
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d258fe61cab24e03a11906615859d3fe
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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