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

HRID 62530

反応式

HRID 62530 の反応式
[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]=[C:17]([Cl:19])[CH:16]=[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:17]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([NH:10][C:6]2[C:5]([Cl:9])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[CH:18]=1

参加物

7

反応物 4

HCID 61695Pentapotassium TriphosphateHCID 170059Benzonitrile, 2-amino-4-chloro-HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 534009652,5-Dichloro-4-iodopyridine

生成物 1

HCID 575169164-Chloro-2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile収率 57.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

To a degassed solution of 2,5-dichloro-4-iodopyridine (4.5 g, 16.43 mmol), 2-amino-4-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 the reflux for 18 hr. The reaction mixture was filtered. The solution was evaporated. Ether (50 ml) was added and the formed solid was filtered. 4-chloro-2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile (2.8 g, 9.38 mmol, 57.1% yield) was isolated as an orange solid. 1H NMR (400 MHz, DMSO-d6) ppm 6.70 (s, 1 H) 7.53 (dd, J=8.34, 2.02 Hz, 1 H) 7.65 (d, J=2.02 Hz, 1 H) 7.95 (d, J=8.34 Hz, 1 H) 8.28 (s, 1 H) 9.12 (br. s., 1 H); HPLC Rt=3.50 min, MS (ESI): 298.0, 300.0 [M+H]+.

後処理

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

出典と根拠

ORDレコード
ord-26a121a17bbd42c3bb2d5e1864966d8f
出典データセット
uspto-grants-2016_09
特許番号
US09446034B2

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