Triethylamine → 7-(5-Methyl-isoxazol-3-yl)-imidazo[1,2-a]pyridine

HRID 341209Notes

Reaction equation

HRID 341209 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10](=O)[C:11]#[C:12][CH3:13])=[CH:6][C:5]=12.Cl.[NH2:16][OH:17].C(N(CC)CC)C>CN(C=O)C>[CH3:13][C:12]1[O:17][N:16]=[C:10]([C:7]2[CH:8]=[CH:9][N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 593208621-Imidazo[1,2-a]pyridin-7-yl-but-2-yn-1-one

Product 1

HCID 593207987-(5-Methyl-isoxazol-3-yl)-imidazo[1,2-a]pyridineYield 25.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-Imidazo[1,2-a]pyridin-7-yl-but-2-yn-1-one (168 mg, 0.91 mmol) and hydroxylamine hydrochloride (94 mg, 1.37 mmol) in DMF (10 ml) was added triethylamine (0.21 ml, 1.83 mmol). The reaction mixture was heated at 80° C. for 18 h, then partitioned between EtOAc and H2O. The organic fraction was separated, dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was purified by silica column chromatography (0-50% MeOH in Et2O) to afford the product (46 mg). MS: [M+H]+=200.

Workup

  1. custompartitioned between EtOAc and H2O
  2. customThe organic fraction was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe crude residue was purified by silica column chromatography (0-50% MeOH in Et2O)

Sources & evidence

ORD record
ord-94248773eb0b4599b3ad1f57941ce58a
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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