Ammonium formate → 2-(7-Ethylimidazo[1,2-a]pyridin-3-yl)quinolin-8-ol

HRID 1095740Notes

Reaction equation

HRID 1095740 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([CH2:28][CH3:29])=[CH:27][C:22]3=[N:21][CH:20]=1)[CH:15]=[CH:14]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].CO>[CH2:28]([C:26]1[CH:25]=[CH:24][N:23]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=4)[N:17]=3)=[CH:20][N:21]=[C:22]2[CH:27]=1)[CH3:29]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 667814498-(Benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinoline

Product 1

HCID 667814032-(7-Ethylimidazo[1,2-a]pyridin-3-yl)quinolin-8-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 8-(benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinoline (3.06 g, 8.06 mmol), Pearlman's catalyst (20% wt Pd, 283 mg) and ammonium formate (5.08 g, 80.6 mmol) in MeOH (50 ml) was degassed under nitrogen and heated at 80° C. for three hours, followed by stirring at ambient temperature overnight. The reaction mixture was poured into excess water and extracted with CH2Cl2 and EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography (eluting with MeOH/CH2Cl2) to afford a mixture of starting material and desired product. This mixture was resubmitted to the original reaction conditions and refluxed for four hours. The reaction mixture was poured into excess water and extracted with CH2Cl2 and EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford the title compound (768 mg, 33% yield) as a solid. MS APCI (+) m/z 290.3 (M+1) detected.

Workup

  1. customwas degassed under nitrogen
  2. additionThe reaction mixture was poured into excess water
  3. extractionextracted with CH2Cl2 and EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (eluting with MeOH/CH2Cl2)
  8. customto afford

Sources & evidence

ORD record
ord-3468e2cbb4e94affb976ed859b4a90b2
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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