Potassium Carbonate → Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate

HRID 335821ノート

反応式

HRID 335821 の反応式
F[C:2]1[N:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([I:25])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.FC(F)(F)S([O-])(=O)=O.[Ag+]>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:2]2[N:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[C:20]([I:25])[CH:19]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 109245324-Bromo-2-iodophenolHCID 67383095Methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate

生成物 1

HCID 67383577Methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

Methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate (1.19 g, 4.85 mmol), 4-bromo-2-iodophenol (1.450 g, 4.85 mmol), and silver trifluoromethanesulfonate (1.496 g, 5.82 mmol) were dissolved in dry THF (40 mL) and treated with potassium carbonate (1.006 g, 7.28 mmol). The mixture was heated to 60° C. for 10 hours before being cooled to rt and filtered through a pad of celite. Water (100 mL) and diethyl ether (100 mL) were added to the filtrate and the phases were separated. The organics were dried with magnesium sulfate, filtered and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to DCM gradient) gave the desired methyl 2-(4-bromo-2-iodophenoxy)-6-fluoro-5-(trimethylsilyl)nicotinate.

後処理

  1. temperaturebefore being cooled to rt
  2. filtrationfiltered through a pad of celite
  3. additionWater (100 mL) and diethyl ether (100 mL) were added to the filtrate
  4. customthe phases were separated
  5. dry with materialThe organics were dried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. customPurification

出典と根拠

ORDレコード
ord-f55f0b01df4b412dbd521f8ed8148d38
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

読み込み中…