Potassium Phosphate, Tribasic → 5-Cyclopropyl-2-fluoropyridine

HRID 401482ノート

反応式

HRID 401482 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1N(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH:9]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=2)[CH2:11][CH2:10]1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 27831685-Bromo-2-fluoropyridine

生成物 1

HCID 576908315-Cyclopropyl-2-fluoropyridine

試薬・触媒・溶媒 2

HCID 178482626HCID 178482626、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-fluoro-5-bromopyridine (1.17 ml, 11.4 mmol), cyclopropylboronic acid (1.47 g, 17.1 mmol) and potassium phosphate (7.26 g, 34.2 mmol) in 1,4-dioxane (20 ml) was stirred under argon atmosphere. Chloro(di-2-norbornylphosphino)(2-dimethylaminoferrocen-1-yl)palladium(II) (67 mg, 0.11 mmol) was added. The reaction mixture was heated at 100° C. under argon atmosphere for 48 hours and then cooled down to room temperature. The crude mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (ISCO Companion|, 80 g column, 0-10% EtOAc/Petroleum ether) to afford the compound (70:30 mixture product:starting material; 1.55 g).

後処理

  1. temperaturecooled down to room temperature
  2. customThe crude mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography (ISCO Companion|, 80 g column, 0-10% EtOAc/Petroleum ether)
  8. customto afford the compound (70:30 mixture product:starting material; 1.55 g)

出典と根拠

ORDレコード
ord-085a84f4b6d2487891d7362e7db87c96
出典データセット
uspto-grants-2014_06
特許番号
US08741931B2

反応ノート

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