Dimethyl Sulfoxide → 3'-fluoro-4'-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

HRID 571060ノート

反応式

HRID 571060 の反応式
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[C:14](=[O:15])[CH:13]=[CH:12][NH:11][CH:10]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].F[C:25]1[C:30]([F:31])=[C:29]([I:32])[CH:28]=[CH:27][N:26]=1.CS(C)=O>C(OCC)(=O)C>[F:31][C:30]1[C:25]([N:11]2[CH:12]=[CH:13][C:14](=[O:15])[C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=3)=[CH:10]2)=[N:26][CH:27]=[CH:28][C:29]=1[I:32]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 114478372,3-Difluoro-4-iodopyridineHCID 674056953-[(4-methoxybenzyl)oxy]pyridin-4(1H)-one

生成物 1

HCID 674184733'-fluoro-4'-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

To a 20 mL microwave vial (Biotage) was added 0.70 g (3.03 mmol) 3-[(4-methoxybenzyl)oxy]pyridin-4(1H)-one, 1.26 g (9.08 mmol) potassium carbonate, 1.10 g (4.54 mmol) 2,3-difluoro-4-iodopyridine and 15 mL DMSO. A yellow suspension formed and the vial was sealed and heated at 85° C. for 48 h on a heat block. The suspension was cooled, diluted with ethyl acetate, and washed twice with 10 mL brine. The organic layer was dried over sodium sulfate, filtered, and evaporated onto silica gel. Purification by flash chromatography (silica gel 0-100% hexanes/EtOAc gradient, followed by 10% MeOH in EtOAc) afforded 3′-fluoro-4′-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2′-bipyridin-4-one as a yellow solid. LCMS (M+H)+ 453.3.

後処理

  1. customA yellow suspension formed
  2. customthe vial was sealed
  3. temperatureThe suspension was cooled
  4. washwashed twice with 10 mL brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated onto silica gel
  8. customPurification by flash chromatography (silica gel 0-100% hexanes/EtOAc gradient, followed by 10% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-629918f3745641f4a06c0cb48f6a16fb
出典データセット
uspto-grants-2015_05
特許番号
US09024032B2

反応ノート

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