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2-Amino-5-bromopyridine → 5-Ethenylpyridin-2-amine

HRID 1792477
Notes
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Reaction equation

HRID 1792477 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:9]([Sn](CCCC)(CCCC)C=C)[CH2:10]CC>C1(C)C(C)=CC=CC=1.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>[CH:9]([C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1)=[CH2:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 81998Tributylvinyltin

Product 1

HCID 220320805-Ethenylpyridin-2-amineYield 45.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

4.13 g 5-bromopyridin-2-yl amine, 7.95 g tributyl(vinyl)tin and 1.38 g tetrakis(triphenylphosphine)palladium were heated in 70 mL xylene at 120° C. for 3 hours under nitrogen atmosphere. The solvent was removed, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate), to give 1.3 g of the title compound as pale yellow crystals.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-95d13c917d1e465a99ea0479340b0bfb
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074801B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes