Dichloromethane → methyl 5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxylate

HRID 521774ノート

反応式

HRID 521774 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=2[F:26])[C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[F:22])=[O:13])[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:35]2[NH:39][CH:38]=[C:37]([C:40]([O:42][CH3:43])=[O:41])[CH:36]=2)O1.C(=O)([O-])[O-].[K+].[K+].ClCCl>O.O1CCOCC1>[F:26][C:25]1[CH:24]=[CH:23][C:11]([C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[F:22])=[O:13])=[CH:10][C:9]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:35]2[NH:39][CH:38]=[C:37]([C:40]([O:42][CH3:43])=[O:41])[CH:36]=2)[CH:7]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 53405106Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrole-3-carboxylateHCID 866515583-(2-Chloropyridin-4-yloxy)-4-fluoro-N-(2-fluoro-5-methylphenyl)benzamide

生成物 1

HCID 51001539methyl 5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-(2-Chloropyridin-4-yloxy)-4-fluoro-N-(2-fluoro-5-methylphenyl)benzamide (1.217 g, 3.25 mmol), methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-3-carboxylate (1.63 g, 6.50 mmol) and potassium carbonate (0.67 g, 4.87 mmol) in water (2.5 mL) and dioxane (15 mL) was purged with nitrogen for several minutes. To the mixture was added tetrakis-triphenylphosphine palladium(0) (0.18 g, (0.16 mmol). The reaction was sealed under nitrogen and heated at 100° C. for 15 h. The cooled reaction was mixed with dichloromethane and filtered through Celite. The red solution was evaporated. The resulting oil was dissolved in dichloromethane, put on a column of silica gel (80 g) and eluted with hexane/EtOAc (1:1) to afford methyl 5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxylate as white solid. Yield: 1.162 g, 77%.

後処理

  1. customwas purged with nitrogen for several minutes
  2. additionTo the mixture was added tetrakis-triphenylphosphine palladium(0) (0.18 g, (0.16 mmol)
  3. customThe reaction was sealed under nitrogen
  4. customThe cooled reaction
  5. filtrationfiltered through Celite
  6. customThe red solution was evaporated
  7. dissolutionThe resulting oil was dissolved in dichloromethane
  8. washeluted with hexane/EtOAc (1:1)

出典と根拠

ORDレコード
ord-ad6428ce33a04669a5adcb35bad78fb5
出典データセット
uspto-grants-2016_05
特許番号
US09328103B2

反応ノート

読み込み中…