3,5-Dibromopyridine → HCID 86679115, compound

HRID 2277650Notes

Reaction equation

HRID 2277650 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=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.CC(C)([O-])C.[Na+]>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]>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([N:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[CH2:3][O:2][CH3:1])[CH:15]=1

Participants

6

Reactant 4

HCID 693693,5-DibromopyridineHCID 634876Binap, (A+-)-HCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 23676156Sodium t-butoxide

Product 1

HCID 86679115HCID 86679115, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

In analogy to the procedure described for the preparation of example 135 [B], (S)-2-methoxymethyl-pyrrolidine was reacted with 3,5-dibromopyridine in the presence of Pd2(dba)3, rac-BINAP and sodium tert-butoxide to give the title compound as a yellow oil. MS: 271.1, 273.1 (M+H+).

Sources & evidence

ORD record
ord-62efb87689424a0188f2d1f39cd07e88
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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