Cesium carbonate → HCID 86624192, compound

HRID 1191159Notes

Reaction equation

HRID 1191159 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.[F:27][C:28]([F:46])([F:45])[CH2:29][S:30][CH2:31][C:32]1([O:44][CH2:43][CH2:42][O:41]1)[C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1.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.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]>[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:13])([F:15])[F:14])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:38][CH2:37][C:36]1[CH:35]=[CH:34][C:33]([C:32]2([O:41][CH2:42][CH2:43][O:44]2)[CH2:31][S:30][CH2:29][C:28]([F:27])([F:45])[F:46])=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495580HCID 58495580, compound

Product 1

HCID 86624192HCID 86624192, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (173 mg, 0.4 mmol) with 4-[2-(2,2,2-trifluoroethylthio)-1,1-(ethylenedioxy)ethyl]-benzylamine (250 mg, 0.8 mmol) using tris(dibenzylideneacetone)dipalladium(0) (73.2 mg, 0.08 mmol), BINAP (106 mg, 0.16 mmol) and cesium carbonate (182 mg, 0.6 mmol) in toluene (20 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (75:25) to give 7-chloro-3-(2,2,2-trifluoroacetyl)-6-{4-[2-(2,2,2-trifluoroethylthio)-1,1-(ethylenedioxy)ethyl]-benzylamino}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (97 mg, 41%).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (75:25)

Sources & evidence

ORD record
ord-238d2e505cf645a4a331fcf0fcd8ca34
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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