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

HRID 1195730Notes

Reaction equation

HRID 1195730 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2].Br[C@@H:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:16]1O.C(=O)([O-])[O-:26].[K+].[K+]>CO.O>[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@@H:16]3[C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:23][C@H:15]3[OH:26])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 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 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 4.4 g (25 mmol) 3-formyl-8-hydroxy-2-methyl-imidazo[1,2-a]pyridine, 10.7 g (50 mmol) (trans)-2-bromo-1-indanol and 13.8 g of potassium carbonate is stirred in 120 ml of methanol/water (4:1) for 16 hours at 40° C. The mixture is worked up analogously to Example 21 and the yield of the title compound m.p. 200°-202° C. (from methanol) is 4.8 g (62%).

Sources & evidence

ORD record
ord-549eaca735cf47ca9d7089df27aa2ed4
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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