Triethylamine → 4-(2-Fluoro-4-nitrophenoxy)-2-(phenoxycarbonylamino)pyridine

HRID 492664ノート

反応式

HRID 492664 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>O1CCCC1>[F:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:27]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:28])[CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine

生成物 1

HCID 231532544-(2-Fluoro-4-nitrophenoxy)-2-(phenoxycarbonylamino)pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine (2.71 g) was dissolved in tetrahydrofuran (60 ml) under a nitrogen atmosphere, and then triethylamine (2.27 ml) and phenyl chloroformate (2.05 ml) were added dropwise thereto while cooling in an ice water bath, followed by stirring at room temperature for 25 min. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to provide a crude product of 4-(2-fluoro-4-nitrophenoxy)-2-(phenoxycarbonylamino)pyridine (5.00 g). The crude product was dissolved in tetrahydrofuran (50 ml), and then pyrrolidine (3.64 ml) was added at room temperature, followed by stirring for 1 hr. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, followed by extracting with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and an brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:2 to 1:4, then ethyl acetate) to provide the titled compound (2.927 g, 78%) as pale brown crystals.

後処理

  1. temperaturewhile cooling in an ice water bath
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure

出典と根拠

ORDレコード
ord-02f0cb3ea12f47c7a9574da79ce9d03a
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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