5-Bromo-2-methylpyridine → HCID 67535208, compound

HRID 1841970Notes

Reaction equation

HRID 1841970 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:9][C:10]([O-:13])(C)[CH3:11].[Na+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:8][C:5]1[N:6]=[CH:7][C:2]([N:6]2[C:9]3[CH:7]=[CH:2][CH:3]=[CH:11][C:10]=3[O:13][CH2:4][CH2:5]2)=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 12010205-Bromo-2-methylpyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 67535208HCID 67535208, compound

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A nitrogen stream was bubbled through a mixture of 5-bromo-2-methylpyridine (3.818 g, 22.195 mmol) in toluene (28 ml), then, tBuONa (6.186 g, 64.365 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.615 g, 1.11 mmol), bis(dibenzylideneacetonato)palladium (0.383 g, 0.666 mmol) and 3,4-dihydro-2H-1,4-benzoxazino [CA.S. 5735-53-5] (1.77 g, 13.097 mmol) were added. The reaction mixture was heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth and washed with EtOAc. The solvent was evaporated in vacuo. The residue was purified by column chromatography (silica gel; eluent:DCM/EtOAc from 100/0 to 80/10 as eluent). The desired fractions were collected and the solvent was evaporated in vacuo to yield intermediate compound D29 (3.812 g, 75%) as a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through diatomaceous earth
  3. washwashed with EtOAc
  4. customThe solvent was evaporated in vacuo
  5. customThe residue was purified by column chromatography (silica gel; eluent:DCM/EtOAc from 100/0 to 80/10 as eluent)
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated in vacuo
  8. customto yield intermediate compound

Sources & evidence

ORD record
ord-4a6949e6cf504e6c975ab05515ca9829
Source dataset
uspto-grants-2015_02
Patent number
US08946205B2

Reaction notes

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