Cesium carbonate → Methyl 7-(3-((2-fluoro-5-methylphenyl)carbamoyl)phenoxy)thieno[3,2-b]pyridine-2-carboxylate

HRID 525834ノート

反応式

HRID 525834 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1.Cl[C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[CH:26]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[S:28][C:21]=12.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[CH:26]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[S:28][C:21]=12)=[O:18]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 28879615N-(2-fluoro-5-methylphenyl)-3-hydroxybenzamideHCID 59424429Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate

生成物 1

HCID 86290415Methyl 7-(3-((2-fluoro-5-methylphenyl)carbamoyl)phenoxy)thieno[3,2-b]pyridine-2-carboxylate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
68 °C

実験手順

A mixture of N-(2-fluoro-5-methylphenyl)-3-hydroxybenzamide (270 mg, 1.1 mmol), methyl 7-chlorothieno[3,2-b]pyridine-2-carboxylate (300 mg, 1.3 mmol) and cesium carbonate (1.0 g, 3.07 mmol) in 10 ml of anhydrous DMSO was heated at 68° C. for 16 hours, cooled to room temperature and partitioned between water (100 ml) and EtOAc (100 ml). The aqueous layer was extracted with more EtOAc (2×50 ml). All the organic layers were combined, washed with brine (50 ml), dried over Na2SO4, and evaporated to dryness to give the crude, which was purified by silica gel chromatography eluted with 1˜2% of MeOH in CHCl3 to give methyl 7-(3-((2-fluoro-5-methylphenyl)carbamoyl)phenoxy)thieno[3,2-b]pyridine-2-carboxylate as light brown oil. Yield: 170 mg, 37%.

後処理

  1. temperaturecooled to room temperature
  2. custompartitioned between water (100 ml) and EtOAc (100 ml)
  3. extractionThe aqueous layer was extracted with more EtOAc (2×50 ml)
  4. washwashed with brine (50 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customto give the crude, which
  8. customwas purified by silica gel chromatography
  9. washeluted with 1˜2% of MeOH in CHCl3

出典と根拠

ORDレコード
ord-886b02cba5bc41daa20bdd4d1c944825
出典データセット
uspto-grants-2016_05
特許番号
US09340555B2

反応ノート

読み込み中…