Methanol → 1-[3-(3-(Pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyridin-7-yl]ethanol

HRID 985520Notes

Reaction equation

HRID 985520 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]=[O:23])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1.[CH3:24][Mg]Br.CO>O1CCCC1>[NH3:1].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]([OH:23])[CH3:24])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 99441283-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehydeHCID 178418573HCID 178418573, compound

Product 2

HCID 222AmmoniaHCID 99228911-[3-(3-(Pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyridin-7-yl]ethanolYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde (100 mg, 0.33 mmol) in tetrahydrofuran (10 ml) was cooled to −78° C. before adding methylmagnesium bromide (1.3 ml of 0.3M solution in diethyl ether) dropwise over 10 min. Once addition was complete the reaction was allowed to warm to ambient temperature and stirring continued for 16 h. Methanol (1 ml) was added and the mixture partitioned between ethyl acetate and 10% ammonium chloride solution. The organic layer was washed with brine, dried over sodium sulphate and concentrated to give a yellow oil. This oil was purified by preparative thin layer chromatography eluting with dichloromethane/methanol/conc. ammonia (95:5:0.5) to afford the title compound (59 mg, 57%) as a white foam. 1H NMR (360 MHz, CDCl3) δH 1.55 (3H, d, J 6), 4.97 (1H, q, J 6), 6.91 (1H, dd, J 2 and 7) 7.37-7.43 (1H, m), 7.56-7.67 (4H, m), 7.65-7.74 (2H, m), 7.89-7.94 (1H, m), 8.33 (1H, d, J 7), 8.60-8.65 (1H, m), 8.89 (1H, s); m/z (ES+) 316 (M++H).

Workup

  1. additionOnce addition
  2. customthe mixture partitioned between ethyl acetate and 10% ammonium chloride solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customThis oil was purified by preparative thin layer chromatography
  8. washeluting with dichloromethane/methanol/conc

Sources & evidence

ORD record
ord-f37837de394d4e878c1b588da6122c80
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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