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

HRID 595798노트

반응식

HRID 595798 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-4c5111933f814b6b9d1e4a3acd4384d0
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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