Cesium carbonate → HCID 59799080, compound

HRID 1013104Notes

Reaction equation

HRID 1013104 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]=1[NH:19][CH2:20][C:21]([CH3:31])([CH3:30])[CH2:22][O:23]C1CCCCO1.ClC1C=CC2CCN(C(=O)C(F)(F)F)CCC=2C=1OS(C(F)(F)F)(=O)=O.CC(C)(COC1CCCCO1)CN.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+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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]>[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:14])([F:13])[F:15])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]([CH3:31])([CH3:30])[CH2:22][OH:23]

Participants

9

Reactant 5

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 57447746HCID 57447746, compoundHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 57447748HCID 57447748, compound

Product 1

HCID 59799080HCID 59799080, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

7-Chloro-6-[2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine Mix 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.277 g, 3.0 mmol), 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propylamine (843 mg, 4.5 mmol), palladium acetate (135 mg, 0.6 mmol), BINAP (1.308 g, 2.1 mmol), bis(dibenzylideneacetone)palladium (0) (275 mg, 0.3 mmol) and cesium carbonate (1.955 g, 6.0 mmol) in anhydrous toluene (75 mL), degas, heat at 90° C. for 16 h. Filter off solid through Celite®, concentrate and purify (silica gel chromatography, eluting with 1:7 EtOAc:hexanes) to give the title compound (1.190 g, 86%).

Workup

  1. customdegas
  2. filtrationFilter off solid through Celite®
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 1:7 EtOAc:hexanes)

Sources & evidence

ORD record
ord-d4aba0e613cd4e5e94e9fe0aed81e71a
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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