Dichloromethane → HCID 59641680, compound

HRID 1867865Notes

Reaction equation

HRID 1867865 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10](Cl)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[Cl:23])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27343222-Chlorophenylboronic acidHCID 59641681HCID 59641681, compound

Product 1

HCID 59641680HCID 59641680, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
70 °C

Procedure

To a flame-dried round bottom flask was placed 2-benzyl-6-chloro-5-(4-chlorophenyl)pyridazin-3(2H)-one (6.0 g, 18.1 mmol), 2-chlorophenylboronic acid (5.7 g, 36.2 mmol), K3PO4 (7.7 g, 36.2 mmol), and [1,1′bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with CH2Cl2 (1:1) (2.96 g, 3.6 mmol). The flask was purged with argon for 15 min before degassed THF (120 mL) was added. The reaction mixture was stirred in a 70° C. oil bath under argon for 16 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc (200 mL), washed with 1N aqueous NaOH (50 mL), H2O, saturated aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (330 g) eluting with a gradient of EtOAc (0-40%) in hexanes to afford 6.5 g (88%) of the title compound as a white solid. HPLC/MS (method A): retention time=3.97 min, (M+H)+=407.0. 1H NMR (CDCl3, 400 MHz): δ 7.51 (d, 2H, J=8.0 Hz), 7.24-7.40 (m, 9H), 6.95-7.03 (m, 3H), 5.33 (s, 2H).

Workup

  1. customTo a flame-dried round bottom flask was placed
  2. customThe flask was purged with argon for 15 min
  3. custombefore degassed THF (120 mL)
  4. additionwas added
  5. temperatureAfter cooling to room temperature
  6. additionthe reaction mixture was diluted with EtOAc (200 mL)
  7. washwashed with 1N aqueous NaOH (50 mL), H2O, saturated aqueous NaCl
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified
  12. washeluting with a gradient of EtOAc (0-40%) in hexanes

Sources & evidence

ORD record
ord-78930eec9d5646e68eb7d2ecfaf710c5
Source dataset
uspto-grants-2009_12
Patent number
US07632837B2

Reaction notes

Loading…