2-Bromopyridine → HCID 89572771, compound

HRID 1621019Notes

Reaction equation

HRID 1621019 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH3:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[C:23]1([C:27]#N)[CH2:26][CH2:25][CH2:24]1.C1C[O:32]CC1>>[CH3:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[C:23]1([C:27]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[O:32])[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 79732-BromopyridineHCID 8028Tetrahydrofuran2×HCID 89525987HCID 89525987, compoundHCID 178418339Butyllithium

Product 1

HCID 89572771HCID 89572771, compoundYield 26.4%

Procedure

To a solution of 2-bromopyridine (449 mg, 2.84 mmol) in THF (10 mL) was added dropwise n-butyl lithium (1.6 N, 1.77 mL, 2.84 mmol) at −78° C. After stirring at the same temperature for 30 minutes, a solution of Example 275B (400 mg, 1.89 mmol) in THF (2 mL) was added. The mixture was stirred at −78° C. for additional 30 minutes and then quenched with aqueous H2SO4 solution (1 N, 5 mL) slowly. The reaction mixture was warmed up to room temperature and partitioned. The aqueous phase was separated and extracted with EtOAc (3×10 mL). The combined organic phases were washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to give the title compound (430 mg, 0.50 mmol, 26.4% yield) as a yellow solid. MS: MS (M+H)+.

Workup

  1. stirringThe mixture was stirred at −78° C. for additional 30 minutes
  2. customquenched with aqueous H2SO4 solution (1 N, 5 mL) slowly
  3. custompartitioned
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc (3×10 mL)
  6. washThe combined organic phases were washed with water (30 mL) and brine (30 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c95434c7135f480a81e4ae43c0942121
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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