3,5-Dibromopyridine → HCID 178455459, compound

HRID 1774726Notes

Reaction equation

HRID 1774726 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:14])([CH3:13])[C@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20](Br)[CH:21]=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:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([N:9]2[CH2:10][CH2:11][CH2:12][C@@H:8]2[C:7]([CH3:14])([CH3:13])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:21]=1

Participants

6

Reactant 4

HCID 693693,5-DibromopyridineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 131734724HCID 131734724, compound

Product 1

HCID 178455459HCID 178455459, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

In analogy to the procedure described for the preparation of intermediate A-3 [B], (R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-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: 371.0, 372.9 (M+H+).

Sources & evidence

ORD record
ord-5a98852b7aae4fdf9e1c6f2033f87b0b
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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