Cesium carbonate → (3-(Diphenylmethyleneamino)-5-(trifluoromethyl)phenyl)(1-methylpiperidin-4-yl)methanone

HRID 2200131Notes

Reaction equation

[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:68]1[CH:69]=[C:70]([C:78]([CH:80]2[CH2:85][CH2:84][N:83]([CH3:86])[CH2:82][CH2:81]2)=[O:79])[CH:71]=[C:72]([C:74]([F:77])([F:76])[F:75])[CH:73]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:2]1([C:1](=[N:14][C:68]2[CH:69]=[C:70]([C:78]([CH:80]3[CH2:81][CH2:82][N:83]([CH3:86])[CH2:84][CH2:85]3)=[O:79])[CH:71]=[C:72]([C:74]([F:75])([F:76])[F:77])[CH:73]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Add benzophenone imine (195 mg, 1.07 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 37 mg, 0.059 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 25 mg, 0.027 mmol] and cesium carbonate (585 mg, 1.79 mmol) to the solution of (3-bromo-5-(trifluoromethyl)phenyl)(1-methylpiperidin-4-yl)methanone (251 mg, 0.717 mmol) in dioxane (5 mL), then stir the reaction mixture overnight at 100° C. Upon reaction completion, filter the mixture and concentrate the filtrate under reduced pressure. Purify the residue with flash chromatography (silica gel, PE:EtOAc=1:1) to afford the product (210 mg, 65%). MS: (M+1): 451.2.

Workup

customUpon reaction completion
filtrationfilter the mixture
concentrationconcentrate the filtrate under reduced pressure
customPurify the residue with flash chromatography (silica gel, PE:EtOAc=1:1)

Sources & evidence

ORD record: ord-bb6bc112e9764ba2a1e8b2fd90eb6aeb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359338B2

Reaction notes

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