4-Methoxybenzylamine → HCID 58016713, compound

HRID 1517086Notes

Reaction equation

HRID 1517086 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:5]=[C:4](OS(C(F)(F)F)(=O)=O)[C:3]=1[C:26]([N:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[CH2:30][CH2:29]1)=[O:27].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:85][O:86][C:87]1[CH:94]=[CH:93][C:90]([CH2:91][NH2:92])=[CH:89][CH:88]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:85][O:86][C:87]1[CH:94]=[CH:93][C:90]([CH2:91][NH:92][C:4]2[C:3]([C:26]([N:28]3[CH2:29][CH2:30][CH:31]([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)[CH2:32][CH2:33]3)=[O:27])=[C:2]([CH3:1])[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)[N:5]=2)=[CH:89][CH:88]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 634876Binap, (A+-)-HCID 86637419HCID 86637419, compound2×

Product 1

HCID 58016713HCID 58016713, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

In analogy to the procedure described for the preparation of example 6, trifluoro-methanesulfonic acid 4-methyl-3-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-6-(3-trifluoromethyl-phenyl)-pyridin-2-yl ester (intermediate 10) was reacted with [rac]-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, palladium(II) acetate and 4-methoxy-benzylamine to give the title compound as yellow oil. MS: 553.4 (MH+).

Sources & evidence

ORD record
ord-8a002aaf23a440ed96138e4ebf02d1e8
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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