Water → 2,5-Dichloro-pyridine-3-carbaldehyde

HRID 11680

Reaction equation

HRID 11680 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C([SnH](CCCC)CCCC)CCC.O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:7][C:8]([Cl:11])=[CH:9][N:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5948TributylstannaneHCID 27999962,5-Dichloro-nicotinoyl chloride

Product 1

HCID 219732742,5-Dichloro-pyridine-3-carbaldehydeYield 34.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-Dichloro-nicotinoyl chloride (15 g, 0.071 mol) in tetrahydrofuran was added tributyl-stannane (24.9 g, 0.086 mol) portionwise over 45 minutes. The resulting mixture was stirred at ambient temperature for 50 minutes, and then treated with tetrakis(triphenylphosphine)palladium(0) (0.82 g, 0.00071 mol). The reaction mixture was stirred at ambient temperature for 4 hours, poured into water; the product was extracted with ethylacetate, the combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate gave the title compound (4.3 g).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 4 hours
  2. extractionthe product was extracted with ethylacetate
  3. dry with materialthe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customSilica gel chromatography (10% ethyl acetate/hexanes) followed by recrystallization from hexanes/ethylacetate

Sources & evidence

ORD record
ord-38c6d934eb854ee7a469257bfdad0650
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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