Pyridine → 3-(3-Fluoro-5-iodopyridin-2-yl)-5,5-dimethyloxazolidin-2-one

HRID 629205Notes

Reaction equation

[F:1][C:2]1[C:3]([NH:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])=[N:4][CH:5]=[C:6]([I:8])[CH:7]=1.N1C=CC=CC=1.[C:21](Cl)(Cl)=[O:22]>ClCCl>[F:1][C:2]1[C:3]([N:9]2[CH2:10][C:11]([CH3:14])([CH3:12])[O:13][C:21]2=[O:22])=[N:4][CH:5]=[C:6]([I:8])[CH:7]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

(580 mg, 1.87 mmol) 1-(3-Fluoro-5-iodopyridin-2-ylamino)-2-methylpropan-2-ol (Example 1, step 1) was dissolved in dichloromethane (10 ml) and pyridine (300 μl, 3.74 mmol, 2 equiv.) was added at room temperature. The mixture was cooled to 0-5° C. and phosgene (20% in toluene) (1.19 ml, 2.24 mmol, 1.2 equiv.) was added dropwise over a period of 15 min at 0-5° C. The mixture was stirred for 1 hour at 0-5° C. The reaction mixture was extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column and eluting with a heptane:ethyl acetate gradient 100:0 to 50:50. The desired 3-(3-fluoro-5-iodopyridin-2-yl)-5,5-dimethyloxazolidin-2-one (500 mg, 1.49 mmol, 79.5% yield) was obtained as a white solid, MS: m/e=337.0 (M+H+).

Workup

extractionThe reaction mixture was extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane
customThe crude product was purified by flash chromatography
washeluting with a heptane

Sources & evidence

ORD record: ord-dbe08e8143134fd39652333314d03b9a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315498B2

Reaction notes

Loading…