10-Phenylphenothiazine

light yellow powder

To a solution of phenothiazine (500 mg, 2.50 mmol) in dry toluene (5 mL) under nitrogen was added iodobenzene (310 mg, 2.2 mmol) sodium tert-butoxide (0.5 mL) and PdPhenothiazine (10 g, 1 eq) and sodium tert-butoxide (14.5 g, 3 eq) were added to a three-necked flask, 100 ml adding iodobenzene of toluene was added, (20.5 g, 2 eq), tris (dibenzylideneacetone) dipalladium (1.15 g, 2 & lt; RTI ID = 0.0 & gt;0.02 eq), tri-tert-butylphosphine (1.62 g, 0.04 eq), ventilated three times, and refluxed overnight at 110 ° C. The TLC test reaction ends with an antiAfter cooling with methylene chloride (100ml), saturated NaCl washing after anhydrous magnesium sulfate drying and drying the organic phase. After the use of oilEther (100 ml) was washed twice to give 10.8 g of pale yellow 10-phenyl-10H-phenothiazine in a yield of 78percent.General procedure: A mixture of N-unsubstituted compound 2 (1.0 mmol), aryl halide 1 (1.2 mmol), and t-BuONa (1.2 mmol) was stirred in DMF (0.3 mL) inthe presence of Cu(OAc)Phenothiazine dissolved 50g (250.9mmol) and bromobenzene, 47.3g (301.1mmol), sodium t- butoxide 36.2g (376.4mmol) and tri -tert- butylphosphine 1.52g (7.53mmol) in toluene 500ml and, after inserting the Pd (dba) 2 1.44g (2.51mmol) and the mixture was stirred under reflux for 6 hours under a nitrogen atmosphere. After the reaction the organic layer was then extracted with ethyl ahseteyiteugwa dry distilled over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product n- hexane / dichloromethane (7: 3 by volume) as a column of silica gel chromatography to obtain the objective compound of the intermediate M-2 61.7 g as a white solid (yield 89percent) .50 g (250.9 mmol) of phenothiazine, 47.3 g (301.1 mmol) of bromobenzene, 36.2 g (376.4 mmol) of sodium t-butoxide, and 1.52 g (7.53 mmol) of tri-tert-butylphosphine were dissolved in 500 ml of toluene, 1.44 g (2.51 mmol) of Pd(dba)2 was added thereto, and the mixture was agitated for 6 hours under a nitrogen atmosphere while being refluxed. When the reaction was complete, the resultant was extracted with ethyl acetate and distilled water, an organic layer obtained therefrom was dried with magnesium sulfate and filtered, and the filtered solution was concentrated under a reduced pressure. The concentrated product was purified with n-hexane/dichloromethane (7:3 of a volume ratio) through silica gel column chromatography, obtaining 61.7 g of a white solid compound, an intermediate M-2 (89percent of a yield).

Molecular Weight:275.4
XLogP3:5.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:275.07687059
Monoisotopic Mass:275.07687059
Topological Polar Surface Area:28.5
Heavy Atom Count:20
Complexity:303
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes