Potassium Phosphate, Tribasic → 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide

HRID 62483

反応式

HRID 62483 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:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][CH3:16])=[O:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([NH:15][CH3:16])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 3080722-Amino-N-methylbenzamideHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 534009652,5-Dichloro-4-iodopyridine

生成物 1

HCID 575168912-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide収率 56.5%

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

A 150-mL sealed tube was charged with 2,5-dichloro-4-iodopyridine (3.5 g, 12.78 mmol), 2-amino-N-methylbenzamide (1.919 g, 12.78 mmol) and tripotassium phosphate (8.14 g, 38.3 mmol) in 1,4-dioxane (100 mL). The reaction mixture was degassed with nitrogen for 10 min. Bis(2-diphenylphosphinophenyl)ether (DPEPhos, 0.688 g, 1.278 mmol) and Pd(OAc)2 (0.115 g, 0.511 mmol) were added and the reaction mixture was heated in a 120° C. oil bath over night. The reaction mixture was filtered through celite, which was washed with dioxane. The solvent was evaporated to dryness and the solid was washed with EtOH (10 mL×3) to give 2.14 g (56%) of product as an off white solid.

後処理

  1. customA 150-mL sealed tube
  2. customThe reaction mixture was degassed with nitrogen for 10 min
  3. filtrationThe reaction mixture was filtered through celite, which
  4. washwas washed with dioxane
  5. customThe solvent was evaporated to dryness
  6. washthe solid was washed with EtOH (10 mL×3)

出典と根拠

ORDレコード
ord-63006ffb9bab4ecca372336ff57f1a83
出典データセット
uspto-grants-2016_09
特許番号
US09446034B2

関連ノート

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