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3-(Tributylstannyl)pyridine → [3,3'-Bipyridine]-2-carbaldehyde

HRID 250975
Notes
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Reaction equation

HRID 250975 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)CCC.Br[C:21]1[C:22]([CH:27]=[O:28])=[N:23][CH:24]=[CH:25][CH:26]=1>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[C:22]=1[CH:27]=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 34838483-(Tributylstannyl)pyridineHCID 164142313-Bromopyridine-2-carbaldehyde

Product 1

HCID 46316053[3,3'-Bipyridine]-2-carbaldehydeYield 29%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-tributylstannanyl-pyridine (255 mg, 0.693 mmol), 3-Bromo-pyridine-2-carbaldehyde (123 mg, 0.660 mmol), and Pd(PPh3)4 (53.1 mg, 0.046 mmol) in toluene (4 mL) was heated to 90° C. for 23 h and cooled to room temperature. The reaction mixture was diluted with EtOAc (50 mL), washed with brine (3×20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (Hexanes/EtOAc, 70:30, then 0:100) afforded [3,3′]Bipyridinyl-2-carbaldehyde (35 mg, 29%) as a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with brine (3×20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography on silica gel (Hexanes/EtOAc, 70:30

Sources & evidence

ORD record
ord-dc8c841dc0f6467b8a0573bbaba0838d
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863293B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes