Potassium Carbonate → 3-(1,3-Oxazol-5-yl)-7-phenylimidazo[1,2-a]pyridine

HRID 1245488Notes

Reaction equation

HRID 1245488 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]3[C:13]([CH:16]=[O:17])=[CH:14][N:15]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S([CH2:28][N+:29]#[C-:30])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CO>[O:17]1[C:16]([C:13]2[N:10]3[CH:11]=[CH:12][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][C:9]3=[N:15][CH:14]=2)=[CH:30][N:29]=[CH:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 219128397-phenyl-Imidazo[1,2-a]pyridine-3-carboxaldehyde

Product 1

HCID 100155073-(1,3-Oxazol-5-yl)-7-phenylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Phenylimidazo[1,2-a]pyridine-3-carbaldehyde (7-1, 0.030 g, 0.14 mmol), tosylmethyl isocyanide (0.032 g, 0.16 mmol) and K2CO3 (0.022 g, 0.16 mmol) were dissolved in 1 ml MeOH and the resulting solution was heated to reflux. After 4 h the reaction was quenched by the addition of water. The resulting mixture was extracted 3× with EtOAc, and the combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography, eluting with a gradient of DCM to 95:5 DCM/MeOH. The product was further purified by reverse phase preparative HPLC to afford the title compound. 1H NMR (CDCl3) δ 8.63 (d, 1H, J=7.1 Hz), 8.52 (s, 1H), 8.27 (s, 1H), 8.25 (s, 1H), 7.78 (m, 2H), 7.74 (dd, 1H, J=1.4, 7.3 Hz), 7.67 (s, 1H), 7.58 (m, 3H). LCMS m/z (M+1) Calc: 262.1, found 262.2.

Workup

  1. temperaturethe resulting solution was heated to reflux
  2. customAfter 4 h the reaction was quenched by the addition of water
  3. extractionThe resulting mixture was extracted 3× with EtOAc
  4. dry with materialthe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography
  8. washeluting with a gradient of DCM to 95:5 DCM/MeOH
  9. customThe product was further purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-fe29ea500a5d41ec992645db1baf28c2
Source dataset
uspto-grants-2006_10
Patent number
US07125888B2

Reaction notes

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