Nitromethane → HCID 59320904, compound

HRID 341205Notes

Reaction equation

HRID 341205 reaction equation
[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1.[N+:13]([CH3:16])([O-:15])=[O:14].C(NCC)C>C1COCC1>[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]([OH:12])[CH2:16][N+:13]([O-:15])=[O:14])=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8021DiethylamineHCID 58081550HCID 58081550, compound

Product 1

HCID 59320904HCID 59320904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 3-Iodo-imidazo[1,2-a]pyridine-7-carbaldehyde (150 mg, 0.54 mmol) in THF (10 ml) was added nitromethane (88 μl, 1.63 mmol), diethylamine (6 μl, 0.05 mmol) and sieves (300 mg). The reaction mixture was heated at 55° C. for 2 hours before being cooled. The sieves were filtered off and the resulting solution partitioned between EtOAc and H2O. The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to afford a crude product that was used as is (116 mg). MS: [M+H]+=334.

Workup

  1. temperaturebefore being cooled
  2. filtrationThe sieves were filtered off
  3. customthe resulting solution partitioned between EtOAc and H2O
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e06989feae5b490f84cbb50f67848899
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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