Potassium Carbonate → 5-(8-Methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-4-yl)oxazole

HRID 1095698Notes

Reaction equation

HRID 1095698 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[N:17]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:21][C:16]3=[N:15][CH:14]=1)[CH:9]=[C:8]2[CH:27]=[O:28].[N+:29]([CH2:31]S(C1C=CC(C)=CC=1)(=O)=O)#[C-:30].C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[N:17]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:21][C:16]3=[N:15][CH:14]=1)[CH:9]=[C:8]2[C:27]1[O:28][CH:31]=[N:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 866386078-Methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline-4-carbaldehyde

Product 1

HCID 667819475-(8-Methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-4-yl)oxazoleYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 8-Methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline-4-carbaldehyde (210 mg, 0.556 mmol) and 1-(isocyanomethylsulfonyl)-4-methylbenzene (130 mg, 0.668 mmol) in MeOH (5 mL) was added K2CO3 (154 mg, 1.11 mmol), followed by heating to reflux for 3 hours. The reaction was then cooled to ambient temperature, concentrated and purified by flash column chromatography (EtOAc/MeOH 10:1) providing the desired product (73%). MS APCI (+) m/z 417.2 (M+1) detected.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (EtOAc/MeOH 10:1)

Sources & evidence

ORD record
ord-66d5cc281d6e4516a0b33983167e5f2a
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

Loading…