3-Bromo-1-phenylpropane-1,2-dione → [6-(1-Hydroxy-1-methylethyl)imidazo[1,2-a]pyridin-2-yl](phenyl)methanone hydrobromide

HRID 600619Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[Br:12][CH2:13][C:14](=O)[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>COCCOCCOC.C1COCC1>[BrH:12].[OH:11][C:8]([C:5]1[CH:4]=[CH:3][C:2]2[N:7]([CH:13]=[C:14]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[N:1]=2)[CH:6]=1)([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 4 °C

Procedure

To a solution of 0.2 g of 2-(6-aminopyridin-3-yl)propan-2-ol in 10 mL of diglyme is added a solution of 0.358 g of 3-bromo-1-phenylpropane-1,2-dione in 5 mL of THF. The reaction mixture is stirred for 15 hours at 4° C. and then concentrated to dryness under reduced pressure. The residue is chromatographed on a column of silica, eluting with dichloromethane and then with a 98/2 mixture of dichloromethane and methanol. The fractions containing the expected product are combined and concentrated to dryness to give 60 mg of [6-(1-hydroxy-1-methylethyl)imidazo[1,2-a]pyridin-2-yl](phenyl)methanone hydrobromide (1:1) in the form of a straw-yellow solid.

Workup

concentrationconcentrated to dryness under reduced pressure
customThe residue is chromatographed on a column of silica
washeluting with dichloromethane
additionwith a 98/2 mixture of dichloromethane and methanol
additionThe fractions containing the expected product
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-5bca0f76aabe498582c0d3159f65b1c8
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902219B2

Reaction notes

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