2-Bromopyridine → 4-(2-Thienyl)pyridine

HRID 1510193Notes

Reaction equation

HRID 1510193 reaction equation
C1COCC1.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[Mg]Br.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C>CCCCCC.C(OCC)(=O)C>[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:18]1[CH:17]=[CH:16][N:15]=[CH:14][CH:19]=1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDEHCID 178418438HCID 178418438, compound

Product 1

HCID 5952454-(2-Thienyl)pyridineYield 94%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using a THF solution of 2-thienylmagnesium bromide (3.00 mL, 1.00 M, 3.0 mmol) and 2-bromopyridine (316.0 mg, 2.0 mmol), CoF2.4H2O (20.3 mg, 0.12 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (102.3 mg, 0.24 mmol) as starting materials, the reaction was performed at a scale of 2.0 mmol at 80° C. for 24 hours in the same manner as in Example 23. After performing silica gel column chromatography (ethyl acetate=5% in hexane), the above compound was obtained as a yellow solid (0.303 g, yield=94%, purity=>98% (GC analysis)).

Workup

  1. customthe above compound was obtained as a yellow solid (0.303 g, yield=94%, purity=>98% (GC analysis))

Sources & evidence

ORD record
ord-6cecb26bcd434e2694f40591154adf00
Source dataset
uspto-grants-2012_07
Patent number
US08211820B2

Reaction notes

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