Cesium carbonate → 4-(2-Amino-thiazol-5-yloxy)-3-fluoro-benzoic acid ethyl ester

HRID 1889176

반응식

HRID 1889176 반응식
Br.Br[C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=1.[CH2:9]([O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=1)[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:9]([O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:3]2[S:7][C:6]([NH2:8])=[N:5][CH:4]=2)=[C:15]([F:20])[CH:14]=1)[CH3:10]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

생성물 1

HCID 596100274-(2-Amino-thiazol-5-yloxy)-3-fluoro-benzoic acid ethyl ester수율 40.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 5-Bromothiazole-2-amine hydrobromide (1.55 g, 5.97 mmol) in acetone (100 mL) was added 3-fluoro-4-hydroxy benzoic acid ethyl ester (1.1 g, 5.97 mmol) and cesium carbonate (3.89 g, 11.94 mmol) under argon atmosphere and refluxed for 5 hrs. The reaction mixture was cooled to room temperature and filtered; the filtrate was concentrated under reduced pressure. The residue was partitioned in between ethyl acetate and water. The layers were separated, the organic layer was washed with cold 2 N NaOH (10 mL), brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide 4-(2-amino-thiazol-5-yloxy)-3-fluoro-benzoic acid ethyl ester (0.68 gm).

후처리

  1. temperaturerefluxed for 5 hrs
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was partitioned in between ethyl acetate and water
  5. customThe layers were separated
  6. washthe organic layer was washed with cold 2 N NaOH (10 mL), brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-60ba5f9922b243679e09b2979a23c471
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501955B2

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