Potassium Carbonate → 3-Formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

HRID 1195731Notes

Reaction equation

HRID 1195731 reaction equation
[OH-].[K+].Br[C@@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]1[OH:13].C(=O)([O-])[O-:15].[K+].[K+].[CH:20]([C:22]1[N:26]2[CH:27]=[CH:28][CH:29]=[C:30](O)[C:25]2=[N:24][C:23]=1[CH3:32])=[O:21]>C(O)(C)C.CO.O>[CH:20]([C:22]1[N:26]2[CH:27]=[CH:28][CH:29]=[C:30]([O:13][C@@H:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:12][C@H:4]3[OH:15])[C:25]2=[N:24][C:23]=1[CH3:32])=[O:21]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 820607(1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-olHCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 228438253-Formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

39.7 ml of 10 N potassium hydroxide solution is added to 85.2 g (400 mmol) (trans)-2-bromo-1-indanol in 600 ml isopropyl alcohol dropwise at room temperature while stirring, and the mixture is stirred for a further 15 minutes at room temperature. The isopropyl alcohol is distilled off at 40° C./5-8 mbar, 350 ml methanol/water (4:1), 30.4 g potassium carbonate and 35.2 g (200 mmol) 3-formyl-8-hydroxy-2-methyl-imidazo[1,2-a]pyridine are added and the mixture is stirred for a further 10 hours at 40° C. and 8 hours at room temperature. The mixture is worked up analogously to Example 21 and the yield of the title compound m.p. 200°-202° C. is 47.2 g (76.5%).

Workup

  1. stirringthe mixture is stirred for a further 15 minutes at room temperature
  2. additionare added
  3. stirringthe mixture is stirred for a further 10 hours at 40° C. and 8 hours at room temperature

Sources & evidence

ORD record
ord-2a7021632c8944e998bee8d9bd1ff79d
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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