Cesium carbonate → HCID 57656180, compound

HRID 911240Notes

Reaction equation

HRID 911240 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.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:79][CH2:80][CH2:81][NH:82][C:83](=[O:89])[O:84][C:85]([CH3:88])([CH3:87])[CH3:86]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCC.CCOC(C)=O.C1(C)C=CC=CC=1>[C:85]([O:84][C:83]([NH:82][CH2:81][CH2:80][NH:79][C:3]1[C:4]2[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6][C:5]=2[CH:17]=[CH:18][C:2]=1[Cl:1])=[O:89])([CH3:88])([CH3:87])[CH3:86]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 187201N-BOC-ethylenediamineHCID 634876Binap, (A+-)-HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 57656180HCID 57656180, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Use a method similar to the General Procedure 5-1, using 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (150 mg, 0.352 mmol), palladium(II) acetate (8 mg, 0.0352 mmol), BINAP (22 mg, 0.0352 mmol), cesium carbonate (163 mg, 0.5 mmol), t-butyl N-(2-aminoethyl)-carbamate (254 mg, 1.59 mmol) and toluene (6 mL) to give, after chromatography on silica gel eluting with hexane/EtOAc (4:1), the desired intermediate (136 mg, 89%).

Workup

  1. customto give

Sources & evidence

ORD record
ord-506ec2cdc99f4d868c481bc10dd22485
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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