Methanol → HCID 59609601, compound

HRID 1660673Notes

Reaction equation

HRID 1660673 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:17])[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][C:10](Br)=[CH:9][CH:8]=3.[C:18]1(B(O)O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CO>C(COC)OC.O.C(Cl)(Cl)Cl>[CH3:17][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)=[CH:11][C:12]=2[S:13][C:14]2[C:5]1=[CH:4][CH:3]=[C:2]([C:26]1[C:27]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:23]=[CH:24][CH:25]=1)[CH:15]=2

Participants

8

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 109156503,7-dibromo-10-methylphenothiazine

Product 1

HCID 59609601HCID 59609601, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

9.30 g (25.1 mmol) of 3,7-dibromo-10-methylphenothiazine, 9.50 g (55.2 mmol) of 1-naphthylboronic acid, 0.407 g (0.50 mmol) of bis(triphenylphosphane)palladium dichloride and 3.80 g (27.5 mmol) of potassium carbonate were heated to boiling under reflux under nitrogen for 5 hours in 204 ml of dimethoxyethane and 101 ml of water. The reaction mixture was cooled to room temperature, stirred further overnight and then filtered. The residue was washed with 470 ml of ethanol and hot water, and dried at 70° C. under reduced pressure. The solid was dissolved in 100 ml of methylene chloride and filtered through silica gel. After the solvent had been removed under reduced pressure, a tacky mass was obtained which, after 200 ml of methanol had been added, crystallized with stirring overnight. The crystals were filtered off with suction, washed with 300 ml of methanol and dried at 40° C. under reduced pressure. 10.33 g of light yellow microcrystals having a melting point of 185-190° C. were obtained. The crude product was recrystallized twice from ethyl acetate. 5.71 g (49% of theory) of analytically pure, almost colorless microcrystals having a melting point of 191-194° C. were obtained, whose solution in chloroform fluoresced at λ=468 nm.

Workup

  1. filtrationfiltered
  2. washThe residue was washed with 470 ml of ethanol and hot water
  3. customdried at 70° C. under reduced pressure
  4. dissolutionThe solid was dissolved in 100 ml of methylene chloride
  5. filtrationfiltered through silica gel
  6. customAfter the solvent had been removed under reduced pressure
  7. customa tacky mass was obtained which
  8. customcrystallized
  9. stirringwith stirring overnight
  10. filtrationThe crystals were filtered off with suction
  11. washwashed with 300 ml of methanol
  12. customdried at 40° C. under reduced pressure
  13. customwere obtained
  14. customThe crude product was recrystallized twice from ethyl acetate
  15. customwere obtained

Sources & evidence

ORD record
ord-9e6756a91516456c96e1e3e0e10ba67a
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

Loading…