Benzylamine → HCID 86629645, compound

HRID 911409Notes

Reaction equation

HRID 911409 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]2[CH2:7][CH2:8][N:9]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:11][C:5]=2[C:4]=1OS(C(F)(F)F)(=O)=O)#[N:2].[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:28]([NH:35][C:4]1[C:5]2[CH2:11][CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:8][CH2:7][C:6]=2[CH:18]=[CH:19][C:3]=1[C:1]#[N:2])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 86629646HCID 86629646, compound

Product 1

HCID 86629645HCID 86629645, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Use a method similar to the General Procedure 5-1 to couple 7-cyano-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (125 mg, 0.3 mmol) with benzylamine (0.1 mL, 0.9 mmol) using palladium(II) acetate (7 mg, 0.03 mmol), BINAP (37 mg, 0.06 mmol) and cesium carbonate (137 mg, 0.4 mmol) in toluene (3 mL). Purify by chromatography on silica gel eluting with heptane/EtOAc (4:1 to 1:1) to give 6-benzylamino-7-cyano-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a clear oil (60 mg, 54%). ES (ES+) m/z: 374 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel eluting with heptane/EtOAc (4:1 to 1:1)

Sources & evidence

ORD record
ord-ef937e724ea14c558d4cdff44cec6c53
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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