Potassium Phosphate, Tribasic → 6-Cyclopropylpyrazine-2-carbonitrile

HRID 931106ノート

反応式

HRID 931106 の反応式
[C:1]([C:3]1[N:8]=[C:7](Cl)[CH:6]=[N:5][CH:4]=1)#[N:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:18]1(B(O)O)[CH2:20][CH2:19]1>O1CCCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:18]1([C:7]2[N:8]=[C:3]([C:1]#[N:2])[CH:4]=[N:5][CH:6]=2)[CH2:20][CH2:19]1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 813036-Chloropyrazine-2-carbonitrileHCID 2760897Cyclopropylboronic acid

生成物 1

HCID 898540196-Cyclopropylpyrazine-2-carbonitrile収率 82%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of 6-cyano-2-chloropyrazine (0.3 g, 2.1 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium (II) (153.6 mg, 0.21 mmol), potassium phosphate (1.3 g, 6.30 mmol) and cyclopropylboronic acid (0.184 mg, 2.1 mmol) in tetrahydrofuran (25 mL, nitrogen bubbled) was degassed for 15 min. using nitrogen. The reaction mixture was refluxed for 16 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 5-20% ethyl acetate in petroleum ether) to afford 6-cyclopropylpyrazine-2-carbonitrile (250 mg, 50%).

後処理

  1. customwas degassed for 15 min.
  2. temperatureThe reaction mixture was refluxed for 16 h
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 5-20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-7e58671c7e634fc59eccd174092cac15
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

読み込み中…