(Pyridin-4-yl)boronic acid → (R)-3'-[4-(4-Pyridyl)thiophen-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

HRID 2109440Notes

Reaction equation

HRID 2109440 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:7]2[CH2:11][C@:10]3([CH:16]4[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]4)[CH2:12]3)[O:9][C:8]2=[O:19])[S:5][CH:6]=1.[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[N:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[C:4]([N:7]3[CH2:11][C@:10]4([CH:16]5[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]5)[CH2:12]4)[O:9][C:8]3=[O:19])[S:5][CH:6]=2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 57634260(R)-3'-(4-Bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Product 1

HCID 11233142(R)-3'-[4-(4-Pyridyl)thiophen-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Procedure

The title compound was prepared by a method analogous to that described in Example 1 from (R)-3′-(4-bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and pyridine-4-boronic acid. The solid obtained after flash chromatography was further purified by reverse phase HPLC on a Phenomenex® Polar RP column using a gradient of 5-45% acetonitrile/water (each solvent containing 0.1% trifluoroacetic acid as a buffer) as the eluant. The residue was partitioned between saturated aqueous potassium carbonate and chloroform and the chloroform layer was dried (magnesium sulfate), filtered and evaporated to give the title compound as a pale solid (74 mg), m/z 342 (MH+).

Workup

  1. customThe title compound was prepared by a method analogous to
  2. customThe solid obtained after flash chromatography
  3. customwas further purified by reverse phase HPLC on a Phenomenex® Polar RP column
  4. additioncontaining 0.1% trifluoroacetic acid as a buffer) as the eluant
  5. customThe residue was partitioned between saturated aqueous potassium carbonate and chloroform
  6. dry with materialthe chloroform layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-081010f5a3fd42cdaa737a16a32ac461
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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