Dimethylformamide → 6-Chloro-5-fluoropyridine-3-carbaldehyde

HRID 2066862

Reaction equation

HRID 2066862 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([F:14])[C:10]([Cl:13])=[N:11][CH:12]=1.CN([CH:18]=[O:19])C.CCOC(C)=O>CCOCC>[Cl:13][C:10]1[N:11]=[CH:12][C:7]([CH:18]=[O:19])=[CH:8][C:9]=1[F:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 27632855-Bromo-2-chloro-3-fluoropyridineHCID 178418339Butyllithium

Product 1

HCID 216981946-Chloro-5-fluoropyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Butyl lithium (2.5 M in hexane, 2.5 mL, 6.3 mmol) was added to 5-bromo-2-chloro-3-fluoro-pyridine (1 g, 4.75 mmol) in 10 mL of ether at −78° C. After 10 minutes, DMF (5 mL) was added and the mixture was warmed to room temperature over 1 h. The mixture was poured into 20 mL of EtOAc and the mixture was washed with water (20 mL) and brine (20 mL), dried over magnesium sulfate and concentrated to afford the crude 53a (0.92 g) as a brown oil: LC-MS160.0 (MH+).

Workup

  1. washthe mixture was washed with water (20 mL) and brine (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c4d725c0dae449cf9394add94b98aae3
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Linked notes

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