Aluminium lithium hydride → HCID 57588508, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (300 mg, 0.89 mmol) in dry THF (9 mL) was added lithium aluminum hydride (1.07 mL, 1.07 mmol, 1.0 M in THF) dropwise at −40° C. under nitrogen. The resulting solution was allowed to slowly warm to −20° C. over the course of 1 hour after which time the reaction was quenched with saturated aqueous ammonium chloride (3 mL) and diluted with ethyl acetate (40 mL). The suspension was filtered through Celite, the filtrate washed with saturated aqueous sodium chloride (20 mL) and then dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material thus isolated was chromatographed over silica gel eluting with MeOH:CH2Cl2 0%→1%→2%) to furnish 40.6 mg (15.5%) of [1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazol-5-yl]methanol EXAMPLE 5. 1H NMR (400 MHz, CDCl3): δ=9.46 (s, 1H), 7.76 (s, 1H), 7.67 (t, J=2.0 Hz, 1H), 7.51-7.49 (m, 1H), 7.47-7.45 (m, 1H), 7.44-7.41 (m, 2H), 7.39-7.35 (m, 2H), 6.16 (d, J=1.2 Hz, 1H), 4.75 (s, 2H). MS (ES+): m/z 296.17 (100) [MH+].

Provenance & Evidence