Cesium carbonate → HCID 86622858, compound

HRID 1013122Notes

Reaction equation

HRID 1013122 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[C:27]1([C:33]2([CH2:38][CH2:39][CH2:40][NH2:41])[O:37][CH2:36][CH2:35][O:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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+]>C1(C)C=CC=CC=1.CCOC(C)=O.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([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:41][CH2:40][CH2:39][CH2:38][C:33]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:34][CH2:35][CH2:36][O:37]1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 23123945HCID 23123945, compoundHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86622858HCID 86622858, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

Place 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (5 g, 11.7 mmol) in toluene (100 mL) with 3-(2-phenyl-[1,3]dioxolan-2-yl)-propylamine (4.85 g, 23.4 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.1 g, 1.17 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binapthyl (5.1 g, 8.19 mmol), palladium acetate (525 mg, 2.34 mmol) and cesium carbonate (5.34 g, 16.38 mmol). Heat for 16 h at 95° C. in a sealed tube. Cool the reaction to RT, dilute with EtOAc (600 mL) and filter. Concentrate the filtrate and chromatograph on silica gel, eluting with 10:90 to 25:75 EtOAc:hexanes to give the title compound contaminated with some colored impurities. Dissolve the residue in 20:80 EtOAc:hexanes (100 mL) and filter to remove solids. Chromatograph the filtrate on silica gel, eluting with 10:90 EtOAc:hexanes to give the title compound as an orange oil (4.32 g, 76%).

Workup

  1. temperatureCool
  2. customthe reaction to RT
  3. filtrationfilter
  4. concentrationConcentrate the filtrate and chromatograph on silica gel
  5. washeluting with 10:90 to 25:75 EtOAc

Sources & evidence

ORD record
ord-cecdc2a9057346b0b76b1b9051f28f4d
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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