Potassium Carbonate → HCID 20781554, compound

HRID 1660672Notes

Reaction equation

HRID 1660672 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)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.C(Cl)(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([C:18]3[CH:23]=[CH:22][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:2]1[CH:3]=[CH:4][CH:5]=[CH:14][CH:15]=1)[CH:15]=2

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 109156503,7-dibromo-10-methylphenothiazine

Product 1

HCID 20781554HCID 20781554, compound

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2.50 g (6.7 mmol) of 3,7-dibromo-10-methylphenothiazine (C. Bodea and M. Terdic, Acad. Rep. Rom. 1962, 13, 81-87), 1.85 g (14.9 mmol) of 98% phenylboronic acid, 0.11 g (0.14 mmol) of bis(triphenylphosphine)palladium dichloride and 1.03 g (7.4 mmol) of potassium carbonate were heated to boiling (75° C.) under reflux under nitrogen for 5 hours in 55 ml of dimethoxyethane and 28 ml of water. The reaction mixture was cooled to room temperature and stirred further overnight. The precipitate was filtered off with suction, washed successively with 125 ml of ethanol and hot water and dried at 70° C. under reduced pressure. The crude product (2.30 g) was heated to boiling under reflux in cyclohexane for two hours. After the hot suspension had been filtered, the residue was dried, dissolved in 40 ml of methylene chloride and filtered through a silica-gel-filled glass fit. After the solvent had been removed, 1.05 g (43% of theory) of light yellow, analytically pure solid having a melting point of 239-241° C. were obtained, whose solution in chloroform fluoresced at λ=464 nm.

Workup

  1. custom(75° C.)
  2. filtrationThe precipitate was filtered off with suction
  3. washwashed successively with 125 ml of ethanol and hot water
  4. customdried at 70° C. under reduced pressure
  5. temperatureThe crude product (2.30 g) was heated
  6. temperatureunder reflux in cyclohexane for two hours
  7. filtrationAfter the hot suspension had been filtered
  8. customthe residue was dried
  9. dissolutiondissolved in 40 ml of methylene chloride
  10. filtrationfiltered through a silica-
  11. additiongel-filled glass fit
  12. customAfter the solvent had been removed
  13. customwere obtained

Sources & evidence

ORD record
ord-feac67004ef7494a8768dbddaa96766a
Source dataset
uspto-grants-2011_10
Patent number
US08029919B2

Reaction notes

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