Formic Acid → 7-fluoro-3,4-dihydro-1,5-naphthyridin-2(1H)-one

HRID 1804717ノート

反応式

HRID 1804717 の反応式
Cl[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.[CH:10](N(C(C)C)CC)([CH3:12])[CH3:11].C(O)=[O:20].C1(C)C=CC=CC=1>C(OCCCC)(=O)C=C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.O>[F:9][C:5]1[CH:6]=[C:7]2[C:2]([CH2:11][CH2:10][C:12](=[O:20])[NH:8]2)=[N:3][CH:4]=1

参加物

8

反応物 4

HCID 284Formic Acid2 回HCID 1140TolueneHCID 81531Diisopropylethylamine2 回HCID 447548682-Chloro-5-fluoropyridin-3-amine

生成物 1

HCID 595107397-fluoro-3,4-dihydro-1,5-naphthyridin-2(1H)-one収率 63.5%

試薬・触媒・溶媒 3

HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒HCID 962Water溶媒HCID 8846Butyl Acrylate溶媒

実験手順

To a suspension of 25.0 g of 2-chloro-5-fluoropyridin-3-amine, 3.8 g of bis(tricyclohexyl phosphine)palladium (II) chloride and 1.5 g of 2-(di-tert-butylphosphino)biphenyl in 75 mL of butyl acrylate, 44.1 g of diisopropylethylamine was added, 15.7 g of formic acid was added dropwise thereto at room temperature, and the mixture was refluxed for 3 hours. To the reaction mixture, 32.1 g of diisopropylethylamine and 11.5 g of formic acid were added at 100° C., and the mixture was refluxed for 5 hours. The reaction mixture was cooled to 80° C., 50 mL of toluene and 75 mL of water were added thereto and the resultant mixture was cooled to room temperature. The solid product was obtained by filtration, and washed using in the order of toluene and water to give 18.0 g of 7-fluoro-3,4-dihydro-1,5-naphthyridin-2(1H)-one as a white solid.

後処理

  1. additionwas added
  2. temperaturethe mixture was refluxed for 5 hours
  3. temperatureThe reaction mixture was cooled to 80° C.
  4. customThe solid product was obtained by filtration
  5. washwashed

出典と根拠

ORDレコード
ord-be03696fb99240869efdb81354ce8fcd
出典データセット
uspto-grants-2013_01
特許番号
US08354426B2

反応ノート

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