2-Fluoro-4-iodopyridine-3-carbaldehyde → HCID 67814875, compound

HRID 2401370Notes

Reaction equation

HRID 2401370 reaction equation
[F:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=[O:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Mg]Br)=[CH:14][CH:13]=1>C1COCC1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:4]([C:3]2[C:2]([F:1])=[N:9][CH:8]=[CH:7][C:6]=2[I:10])[OH:5])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 99923282-Fluoro-4-iodopyridine-3-carbaldehydeHCID 178478191HCID 178478191, compound

Product 1

HCID 67814875HCID 67814875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-4-iodonicotinaldehyde (1.50 g, 5.98 mmol) in anhydrous THF (20 mL) at −78° C. was slowly added a solution of (4-chlorophenyl)magnesium bromide (1 M in Et2O) (6.57 mL, 6.57 mmol). After 15 minutes at −78° C., the reaction was quenched with MeOH followed by saturated aqueous ammonium chloride, and the product was extracted with CH2Cl2 (4×). The organic layers were combined, dried over a cotton plug and concentrated to dryness under vacuum. The residue was used without any purification in the next step. LC/MS m/z 364 [M+H]+.

Workup

  1. customthe reaction was quenched with MeOH
  2. extractionthe product was extracted with CH2Cl2 (4×)
  3. customdried over a cotton plug
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue was used without any purification in the next step

Sources & evidence

ORD record
ord-b06cca8b52b04f6d84b11ddf74676e4b
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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