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

HRID 931106노트

반응식

HRID 931106 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 898540196-Cyclopropylpyrazine-2-carbonitrile수율 82%

시약·촉매·용매 2

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

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7e58671c7e634fc59eccd174092cac15
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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