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

HRID 1966560ノート

反応式

HRID 1966560 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 6371PhosgeneHCID 575167121-(3-Fluoro-5-iodopyridin-2-ylamino)-2-methylpropan-2-ol

生成物 1

HCID 575167133-(3-Fluoro-5-iodopyridin-2-yl)-5,5-dimethyloxazolidin-2-one収率 79.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
2.5 °C

実験手順

(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+).

後処理

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

出典と根拠

ORDレコード
ord-37e486f150fa4f7aa3df78e369622d5e
出典データセット
uspto-grants-2013_04
特許番号
US08420661B2

反応ノート

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