2-Bromo-6-methylpyridine → HCID 59007075, compound

HRID 130406Notes

Reaction equation

HRID 130406 reaction equation
C[Sn](C)(C)[C:3]1[S:7][C:6]([S:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:5][CH:4]=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1>CN1CCCC1=O.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:27][C:23]1[N:22]=[C:21]([C:3]2[S:7][C:6]([S:8]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:10])=[O:9])=[CH:5][CH:4]=2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 2

HCID 792052-Bromo-6-methylpyridineHCID 86200889HCID 86200889, compound

Product 1

HCID 59007075HCID 59007075, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of phenyl 5-(trimethylstannanyl)-2-thiophenesulfonate (1.3 g, 3.2 mmol) (WO 9827069), 2-bromo-6-methylpyridine (550 mg, 3.2 mmol) and dichlorobis(triphenylphosphine)palladium (II) (100 mg) in 1-methyl-2-pyrrolidinone (10 ml) was heated at 90° C. under argon for 4 hours. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography (1:10 ethyl acetate:pentane) to afford the title product (D11). MS (ES+) m/e 332 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (1:10 ethyl acetate:pentane)

Sources & evidence

ORD record
ord-6641197343014445b5322bab0d2d6607
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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