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

HRID 525834노트

반응식

HRID 525834 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
68 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-886b02cba5bc41daa20bdd4d1c944825
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340555B2

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