Tetrahydrofuran → HCID 89690289, compound

HRID 2202994Notes

Reaction equation

HRID 2202994 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH3:15])=[C:11]([CH:13]=O)[N:12]=2)[CH:9]=1.[CH2:16]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:13]([C:11]1[N:12]=[C:7]2[CH:6]=[CH:5][C:4]([I:3])=[CH:9][N:8]2[C:10]=1[CH3:15])=[CH2:16]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 89690255HCID 89690255, compound

Product 1

HCID 89690289HCID 89690289, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of methyltriphenylphosphonium bromide (3.1 g) in THF (20 ml) was added NaH (60% in oil, 336 mg) at 0° C. The reaction mixture was then stirred at room temperature for 16 h. A solution of 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carbaldehyde (500 mg) in THF (10 ml) was added to the reaction mixture at 0° C., and the resulting mixture was stirred at room temperature for 4 h. The reaction mixture was quenched with ice-water (20 ml) and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (hexane/EtOAc) to afford the title compound (350 mg) as an off-white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 4 h
  2. customThe reaction mixture was quenched with ice-water (20 ml)
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-d3d76c06e4874ecab4cf3b088d377d78
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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