Acetamide → N-(4-((4-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

HRID 626517ノート

反応式

HRID 626517 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[N:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:19]([NH2:22])(=[O:21])[CH3:20].C([O-])([O-])=O.[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[N:13]=[CH:14][C:9]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:22][C:19](=[O:21])[CH3:20])[CH:7]=1

参加物

8

反応物 4

HCID 178AcetamideHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866416892-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine

生成物 1

HCID 90409722N-(4-((4-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide収率 64%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A solution of 5-((2-chloropyridin-4-yl)oxy)-4-methyl-2-nitropyridine (0.52 g, 1.957 mmol) in dioxane (15 mL) was sparged with Ar, treated with acetamide (0.347 g, 5.87 mmol), Cs2CO3 (0.638 g, 1.957 mmol), X-Phos (0.093 g, 0.196 mmol) and Pd2(dba)3 (0.179 g, 0.196 mmol) and heated at 90° C. overnight. The mixture was cooled to RT, diluted with EtOAc, the solids removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/DCM) to afford N-(4-((4-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (360 mg, 64%). 1H NMR (400 MHz, DMSO-d6): δ 10.66 (s, 1H), 8.47 (s, 1H), 8.43 (s, 1H), 8.24 (d, J=5.7 Hz, 1H), 7.72 (d, J=2.4 Hz, 1H), 6.74 (dd, J=5.7, 2.4 Hz, 1H), 2.33 (s, 3H), 2.05 (s, 3H); MS (ESI) m/z: 289.1 (M+H+).

後処理

  1. temperatureThe mixture was cooled to RT
  2. customthe solids removed via filtration through diatomaceous earth
  3. washwashed with EtOAc
  4. washthe filtrate was washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (EtOAc/DCM)

出典と根拠

ORDレコード
ord-9cc56f0fa839471ca3e0ea56193529d7
出典データセット
uspto-grants-2016_04
特許番号
US09309224B2

反応ノート

読み込み中…