Triethylamine → 8-(trans-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053041Notes

Reaction equation

[OH:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([CH2:8][O:9][CH3:10])[CH:7]=1.[O:16]1[CH:18]2[CH2:19][C:20]3[C:25]([CH:17]12)=[CH:24][CH:23]=[CH:22][CH:21]=3.C(N(CC)CC)C.[Cl-].[NH4+]>CO.O>[OH:16][C@@H:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:17]1[O:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([CH2:8][O:9][CH3:10])[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 1.0 g (4.9 mmol) 8-hydroxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine and 1.3 g (9.7 mmol) 1,2-epoxyindane in 12 ml methanol and 3 ml water are added 1.4 ml triethylamine and the mixture is heated to 50° C. for 24 h. After cooling down, the reaction mixture is poured into 100 ml saturated aqueous ammonium chloride and extracted with dichloromethane. The organic phase is dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (20:1) yields 0.7 g (45%) of the title compound as a colourless solid (m.p. 142-143° C.).

Workup

temperatureAfter cooling down
extractionextracted with dichloromethane
dry with materialThe organic phase is dried over anhydrous magnesium sulphate
customevaporated
customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record: ord-4d04100cd3e3490c9035f70b725cb50f
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326718B2

Reaction notes

Loading…