Iodine → HCID 89421783, compound

HRID 1481782Notes

Reaction equation

HRID 1481782 reaction equation
[Cl:1][C:2]1[N:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[Li+].CC([N-]C(C)C)C.[I:27]I>C1COCC1>[Cl:1][C:2]1[N:17]=[CH:16][C:15]([I:27])=[C:14]([Cl:18])[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 89421761HCID 89421761, compound

Product 1

HCID 89421783HCID 89421783, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Into a solution of benzyl 2,4-dichloronicotinate (4.35 g, 15.4 mmol) in THF (40 mL) at −78° C. was added LDA (1.5 M×11.8 mL, 17.7 mmol) dropwise. The mixture was stirred at −78° C. for 30 min. Iodine (4.7 g, 18.5 mmol) was added portionwise. The temperature was then allowed to rise to room temperature slowly and the reaction was quenched with saturated NH4Cl solution. The mixture was extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, evaporated and purified by silica chromatography (0-7% ethyl acetate in hexanes) to give benzyl 2,4-dichloro-5-iodonicotinate (3.8 g, 60%).

Workup

  1. customto rise to room temperature
  2. customthe reaction was quenched with saturated NH4Cl solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. custompurified by silica chromatography (0-7% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5190c7e24b6f436cb10d3d8f616637cf
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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