4-(Tri-n-butylstannyl)pyridine → HCID 57634258, compound

HRID 2109470Notes

Reaction equation

HRID 2109470 reaction equation
Br[C:2]1[N:3]=[C:4]([N:8]2[CH2:12][C@:11]3([CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)[O:10][C:9]2=[O:20])[S:5][C:6]=1Br.C([Sn](CCCC)(CCCC)[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)CCC>>[N:29]1[CH:30]=[CH:31][C:26]([C:2]2[N:3]=[C:4]([N:8]3[CH2:12][C@:11]4([CH:17]5[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]5)[CH2:13]4)[O:10][C:9]3=[O:20])[S:5][CH:6]=2)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 27373184-(Tri-n-butylstannyl)pyridineHCID 69060731HCID 69060731, compound

Product 1

HCID 57634258HCID 57634258, compound

Procedure

The title compound was prepared by a method analogous to that described in Example 14 from the reaction of the mixture of(R)-3′-(4-bromothiazol-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and (R)-3′-(4,5-dibromothiazol-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one with 4-(tri-n-butylstannyl)pyridine. Separation by reverse phase HPLC separation followed by conversion to the free base as described in Example 14 to give the title compound, m/z 343 (MH+); and (R)-3′-[4,5-di(4-pyridyl)thiazol-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one, m/z 420 (MH+).

Workup

  1. customThe title compound was prepared by a method analogous to
  2. customSeparation by reverse phase
  3. customHPLC separation

Sources & evidence

ORD record
ord-0875bb2800cb4d0182725659e670e3e6
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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