Cesium carbonate → HCID 86629636, compound

HRID 911398Notes

Reaction equation

HRID 911398 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.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH2:34].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>[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:34][CH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 195092-PyridinemethanamineHCID 634876Binap, (A+-)-HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86629636HCID 86629636, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Use a method similar to the General Procedure 5-1 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (500 mg, 1.17 mmol) with pyridin-2-ylmethylamine (254 mg, 2 equiv.) using palladium acetate (0.1 equiv.), BINAP (0.3 equiv.) and cesium carbonate (1.4 equiv.) in toluene (5 mL). Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (10:1, 5:1, 3:1, and 1:1) to give 7-chloro-6-(pyridin-2-ylmethylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil.

Workup

  1. customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (10:1, 5:1, 3:1, and 1:1)

Sources & evidence

ORD record
ord-ce489afac9544af3b9155422e5222606
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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