Tetrahydrofuran → Methyl 2-[3-(hydroxymethyl)imidazo[1,2-a]pyridin-2-yl]-1-naphthoate

HRID 1047180Notes

Reaction equation

HRID 1047180 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:22]([O:24][CH3:25])=[O:23])=[O:2].O1CCCC1.[BH4-].[Na+].[Cl-].[NH4+]>O>[OH:2][CH2:1][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86664122Methyl 2-(3-formylimidazo[1,2-a]pyridin-2-yl)-1-naphthoate

Product 1

HCID 67283613Methyl 2-[3-(hydroxymethyl)imidazo[1,2-a]pyridin-2-yl]-1-naphthoateYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound prepared in Example 4 (195 mg) was added to tetrahydrofuran (1.5 mL) and suspended. A solution of sodium borohydride (34 mg) in water (0.4 mL) was added to the reaction mixture on ice bath, and the reaction mixture was stirred for an hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the reaction mixture was extracted twice with ethyl acetate. The obtained organic layer was joined, and washed with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated salt solution sequentially. The obtained organic layer concentrated under reduced pressure after drying with anhydrous sodium sulfate. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=25:75) to give the title compound (186 mg) having the following physical data.

Workup

  1. extractionthe reaction mixture was extracted twice with ethyl acetate
  2. washwashed with water
  3. concentrationThe obtained organic layer concentrated under reduced pressure
  4. dry with materialafter drying with anhydrous sodium sulfate
  5. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=25:75)

Sources & evidence

ORD record
ord-76eb114ace9e4d7bbd71ae8a319b5c0e
Source dataset
uspto-grants-2013_10
Patent number
US08569504B2

Reaction notes

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