Benzylethanolamine → N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

HRID 595798ノート

反応式

HRID 595798 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:11])[CH:3]=1.CCN(C(C)C)C(C)C.[CH2:21]([NH:28][CH2:29][CH2:30][OH:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([N:28]([CH2:29][CH2:30][OH:31])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[F:11])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 4348BenzylethanolamineHCID 81531DiisopropylethylamineHCID 27340264-Bromo-2-fluorobenzoyl chloride

生成物 1

HCID 60740299N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-bromo-2-fluorobenzoyl chloride (1 g, 4.21 mmol) in THF (14.04 mL) was added DIEA (1.103 mL, 6.32 mmol) and 2-(benzylamino)ethanol (0.764 g, 5.05 mmol) at room temperature. The reaction mixture was stirred for overnight. The reaction mixture was extracted with EtOAc. The organic layer was washed with water and brine. After dried over anhydrous sodium sulfate, filtered and concentrated in vacuo, the crude N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide was used for the next step (83%). LCMS (m/z): 352/354 (MH+), 0.83 min.

後処理

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialAfter dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custom352/354 (MH+), 0.83 min.

出典と根拠

ORDレコード
ord-4c5111933f814b6b9d1e4a3acd4384d0
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

読み込み中…