Aluminium lithium hydride → 2-Hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

HRID 586371Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[C:19]([O-])=[O:20])[CH2:8][CH3:9]>C1COCC1>[OH:20][CH2:19][C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[C:10]=1[CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of LiAlH4 (1M in THF, 4.0 mL, 4.0 mmol) is added to a solution of 3-(1-propyl)-imidazolo[1,2-a]pyridine-2-carboxylate (1 g, 4.3 mmol) in anhydrous THF (50 mL) at 0° C. under nitrogen with magnetic stirring. The resulting pale yellow solution is stirred at 0° C. for 4 h and then quenched by addition of 75 mL of EtOAc and 2 mL saturated aqueous Na2SO4. The resulting mixture is stirred for 1 hour at ambient temperature, dried over anhydrous Na2SO4, filtered through celite and evaporated at reduced pressure to obtain 2-hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine as a colorless film. TLC (10% MeOH/CH2Cl2) Rf=0.15. Step 4. Preparation of 2-chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

Workup

customquenched by addition of 75 mL of EtOAc and 2 mL saturated aqueous Na2SO4
stirringThe resulting mixture is stirred for 1 hour at ambient temperature
dry with materialdried over anhydrous Na2SO4
filtrationfiltered through celite
customevaporated at reduced pressure

Sources & evidence

ORD record: ord-47385daba3d94febb03d04e3eb4e8545
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936617B2

Reaction notes

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