Pentapotassium Triphosphate → 5-Chloro-2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile

HRID 62533

반응식

HRID 62533 반응식
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:12]=1[C:13]#[N:14].[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:11]([NH:10][C:6]2[C:5]([Cl:9])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[C:12]([CH:15]=1)[C:13]#[N:14]

참가 물질

7

반응물 4

HCID 61695Pentapotassium TriphosphateHCID 800192-Amino-5-chlorobenzonitrileHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 534009652,5-Dichloro-4-iodopyridine

생성물 1

HCID 575169175-Chloro-2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile수율 33%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

To a degassed solution of 2,5-dichloro-4-iodopyridine (4.5 g, 16.43 mmol), 2-amino-5-chlorobenzonitrile (2.507 g, 16.43 mmol) and potassium triphosphate (10.46 g, 49.3 mmol) in 1,4-dioxane (60 ml) stirred under nitrogen at the room temperature was added DPEPhos (0.708 g, 1.314 mmol) and palladium acetate (0.148 g, 0.657 mmol). The reaction mixture was stirred at reflux for 18 hr. The reaction mixture was filtered. The reaction mixture was evaporated. Ether (50 ml) was added and the solid was filtered. 5-chloro-2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile (1.8 g, 5.43 mmol, 33.0% yield) was isolated as orange solid. 1H NMR (400 MHz, DMSO-d6) ppm 6.63 (s, 1 H) 7.52 (d, J=8.59 Hz, 1 H) 7.81 (dd, J=8.59, 2.53 Hz, 1 H) 8.09 (d, J=2.53 Hz, 1 H) 8.24 (s, 1 H) 9.06 (br. s., 1 H); HPLC Rt=3.53 min, MS (ESI): 298.0, 299.9 [M+H]+.

후처리

  1. temperatureat reflux for 18 hr
  2. filtrationThe reaction mixture was filtered
  3. customThe reaction mixture was evaporated
  4. additionEther (50 ml) was added
  5. filtrationthe solid was filtered

출처 및 근거

ORD 기록
ord-54da0cd2dccb47709c1b181e15a3543d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446034B2

연결된 노트

불러오는 중…