3-Bromopyridine → 3-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonane

HRID 914761Notes

Reaction equation

HRID 914761 reaction equation
[CH:1]12[CH2:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][NH:3][CH2:2]2.Br[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=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([O-])(C)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]>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N:3]2[CH2:4][CH:5]3[CH2:9][CH:1]([CH2:8][NH:7][CH2:6]3)[CH2:2]2)[CH:12]=1

Participants

6

Reactant 4

HCID 122863-BromopyridineHCID 1927203,7-Diazabicyclo(3.3.1)nonaneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 99206863-(3-Pyridinyl)-3,7-diazabicyclo[3.3.1]nonaneYield 25%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

3,7-Diazabicyclo[3.3.1]nonane, prepared as described in (Garrison, G. L. et. al., J. Org. Chem. 58, 27, (1993) 7670), and 3-bromopyridine were processed as described in Example 1A. The proportions of reagents were changed from Example 1A to the following: Pd2(dba)3 (0.02 eq), BINAP (0.05 eq), and NaOt-Bu (1.7 eq). The title compound was obtained in 25% yield after purification by flash chromatography (silica gel; CHCl3:MeOH:NH4OH; 90:5:1). MS (DCI/NH3) m/z 204 (M+H)+.

Sources & evidence

ORD record
ord-6811a3758a684bb1a9697c9923b6bd4d
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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