Sodium hydride → 8-chloro-5-vinyl-5H-chromeno[3,4-c]pyridine

HRID 870909Notes

Reaction equation

HRID 870909 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:16]([OH:19])[CH:17]=[CH2:18])=[C:6](F)[CH:5]=1>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[CH:16]([CH:17]=[CH2:18])[O:19][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 866959021-(4-(4-Chloro-2-fluorophenyl)pyridin-3-yl)prop-2-en-1-ol

Product 1

HCID 866959038-chloro-5-vinyl-5H-chromeno[3,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of NaH (0.182 g, 7.58 mmol) in THF (30 mL) was added 1-(4-(4-chloro-2-fluorophenyl)pyridin-3-yl)prop-2-en-1-ol (0.5 g, 1.896 mmol) dissolved in THF (5 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction was quenched by addition of saturated aqueous ammonium chloride solution (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine (1×10 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude 8-chloro-5-vinyl-5H-chromeno[3,4-c]pyridine was used without purification in the next step.

Workup

  1. customThe reaction was quenched by addition of saturated aqueous ammonium chloride solution (5 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic extracts were washed with brine (1×10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude 8-chloro-5-vinyl-5H-chromeno[3,4-c]pyridine was used without purification in the next step

Sources & evidence

ORD record
ord-4e1f8cdd540e40c6a5017f8d7c17abc9
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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