Potassium Carbonate → HCID 131735698, compound

HRID 2199629Notes

Reaction equation

[I:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[CH:7]=1.Br[CH2:14][CH2:15][CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Si:18]([O:17][CH2:16][CH2:15][CH2:14][N:10]1[N:11]=[N:12][C:8]([C:6]2[CH:5]=[N:4][CH:3]=[C:2]([I:1])[CH:7]=2)=[N:9]1)([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

The reaction mixture of 3-iodo-5-(2H-tetrazol-5-yl)pyridine (273 mg, 1 mmol, 1 eq), (3-bromopropoxy)-tert-butyldimethylsilane (0.31 mL, 1.3 eq), potassium carbonate (207 mg, 1.5 eq) in anhydrous DMF (4 mL) under nitrogen atmosphere was stirred and heated at 80° C. for 5 hours. The mixture was then diluted with ethyl acetate, washed sequentially with saturated aqueous sodium bicarbonate, aqueous ammonium chloride, brine, and dried with anhydrous sodium sulfate. The upper liquor was decanted, concentrated under reduced pressure, and the resulting brown oily residue was subject to a gradient column chromatography (EtOAc-Hex 1:50 to 1:4) giving 3-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)-5-iodopyridine as a soft white solid in the amount of 395 mg.

Workup

washwashed sequentially with saturated aqueous sodium bicarbonate, aqueous ammonium chloride, brine
dry with materialdried with anhydrous sodium sulfate
customThe upper liquor was decanted
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a7d82141efe44ca4874aca5a1d723e82
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359336B2

Reaction notes

Loading…