2-Bromopyridine → HCID 21706291, compound

HRID 1594879Notes

Reaction equation

HRID 1594879 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][C:15]=1[F:22]>C1COCC1>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[OH:19])=[CH:16][C:15]=1[F:22]

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 21706291HCID 21706291, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of n-butyllithium (2.5 M/hexane, 0.98 mL, 2.46 mmol) in THF (7 mL) at −78° C. was added 2-bromopyridine (0.235 mL, 2.46 mmol) dropwise. The mixture was stirred at −78° C. for 1 hr. This solution was added via cannula to a solution of 4-bromo-3-fluorobenzaldehyde (as described in Example 20, Step A) (0.5 g, 2.46 mmol) in THF (5 mL) at −78° C. The resulting solution was stirred at −78° C. for 15 min. and at 25° C. for 2 hr. The reaction was cooled to 0° C. and quenched with saturated NH4Cl. The mixture was partitioned with EtOAc and the organic layer was washed with water, brine and dried over MgSO4. The solvents were removed in vacuo to obtain the title compound after chromatography (silica gel, CH2Cl2:MeOH 99:1).

Workup

  1. stirringThe resulting solution was stirred at −78° C. for 15 min. and at 25° C. for 2 hr
  2. temperatureThe reaction was cooled to 0° C.
  3. customquenched with saturated NH4Cl
  4. customThe mixture was partitioned with EtOAc
  5. washthe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-3b4765f49cc44f95b141c9c84025ed2d
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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