2-Bromo-5-methylpyridine → HCID 20092982, compound

HRID 274576Notes

Reaction equation

HRID 274576 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C([Li])CCC.FC(F)(F)S(O[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]#[N:27])(=O)=O>C1COCC1.CCCCCC.[Cl-].[Zn+2].[Cl-].[Zn].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>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[N:3][CH:4]=1

Participants

9

Reactant 3

HCID 5642162-Bromo-5-methylpyridineHCID 11196048138313-23-2HCID 178418339Butyllithium

Product 1

HCID 20092982HCID 20092982, compound

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of 2-bromo-5-methylpyridine (1.2 g) in THF (15 ml) at -78° C. under argon atmosphere was added 1.65M solution of butyl lithium in hexane (4.4 ml) dropwise and the reaction mixture was stirred for 10 minutes followed by addition of zinc chloride (1M ether solution, 7.2 ml) and then stirring at 0° C. for 30 minutes. The resulting zinc compound was poured into an ice-cooled, stirred mixture of 2-cyanophenyl trifluoromethanesulfonate (1.2 g) and tetrakistriphenylphosphine paladium (Pd(PPh3)4, 0.42 g) in THF (15 ml) under argon atmosphere and the mixture was stirred for 15 hours and concentrated to dryness. The residue was purified by column chromatography on silica gel to give crystals. Recrystallization from hexane afforded colorless needles (0.4 g, 29%), m.p. 80°-81° C.

Workup

  1. stirringstirring at 0° C. for 30 minutes
  2. temperaturecooled
  3. stirringstirred
  4. stirringthe mixture was stirred for 15 hours
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography on silica gel
  7. customto give crystals
  8. customRecrystallization from hexane afforded colorless needles (0.4 g, 29%), m.p. 80°-81° C.

Sources & evidence

ORD record
ord-c3975a8e306d4041affe067fe7eb2de5
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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