Cesium carbonate → 6-(Spiro[4.5]dec-7-ylmethoxy)-pyridine-3-carboxaldehyde

HRID 2070602Notes

Reaction equation

HRID 2070602 reaction equation
C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:36]1[C:40]2([CH2:45][CH2:44][CH2:43][CH:42]([CH2:46][OH:47])[CH2:41]2)[CH2:39][CH2:38][CH2:37]1.Br[C:49]1[N:54]=[CH:53][C:52]([CH:55]=[O:56])=[CH:51][CH:50]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:36]1[C:40]2([CH2:45][CH2:44][CH2:43][CH:42]([CH2:46][O:47][C:49]3[N:54]=[CH:53][C:52]([CH:55]=[O:56])=[CH:51][CH:50]=3)[CH2:41]2)[CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 57771578Spiro[4.5]dec-7-yl-methanol

Product 1

HCID 577714876-(Spiro[4.5]dec-7-ylmethoxy)-pyridine-3-carboxaldehydeYield 19.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of palladium(II) acetate (135 mg), 2-(di-tert-butylphosphino)-1,1′-binaphthyl (478 mg) and cesium carbonate (3.9 g) was added toluene (15 mL), followed by stirring under argon atmosphere at room temperature for 10 minutes. To this reaction mixture were added spiro[4.5]dec-7-yl-methanol (1.0 g) obtained in Step 1 and 6-bromopyridine-3-carboxaldehyde (1.1 g), followed by stirring the mixture at 90° C. for 1.5 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:49 to 1:9) to give 6-(spiro[4.5]dec-7-ylmethoxy)-pyridine-3-carboxaldehyde (0.313 g).

Workup

  1. stirringby stirring the mixture at 90° C. for 1.5 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:49 to 1:9)

Sources & evidence

ORD record
ord-ad59ce1692d840ec8ac221fa6cc568e3
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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