Ammonium formate → 2-[3-(2-Trimethylsilylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]-ethanol

HRID 377224Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

6-Oxiranyl-3-(2-trimethylsilylethoxymethyl)-3H-imidazo-[4,5-b]pyridine (918 mg, 3.15 mmol) was combined with 10% Pd/C (400 mg) and ammonium formate (993 mg, 15.75 mmol) and the mixture was suspended in methanol (25 mL). The reaction mixture was heated to 70° C. for 2.5 h. After cooling to ambient temperature, the mixture was filtered through celite®, eluted with methanol, concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel using 75% ethyl acetate/hexanes then 95.5 CH2Cl2 /MeOH as the eluents, which provided 480 mg of the title compound (43% yield for 3 steps).

Workup

temperatureAfter cooling to ambient temperature
filtrationthe mixture was filtered through celite®
washeluted with methanol
concentrationconcentrated in vacuo
customThe crude residue was purified by flash chromatography on silica gel using 75% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-bc92fd30f8994ce3879242acb66422e2
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06025366

Reaction notes

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