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

HRID 1889176ノート

反応式

HRID 1889176 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-60ba5f9922b243679e09b2979a23c471
出典データセット
uspto-grants-2013_08
特許番号
US08501955B2

反応ノート

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