Tetrahydrofuran → (S)-1-(1-{[4-(3-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422485노트

반응식

HRID 2422485 반응식
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[N+:23]([C:26]1[CH:43]=[CH:42][C:29]([C:30]([O:32][C:33]([CH2:40][CH3:41])([C:36]([F:39])([F:38])[F:37])[C:34]#[CH:35])=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].C1COCC1>C(OCC)(=O)C.[Cu](I)I>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][C@@:33]([C:34]2[N:3]=[N:2][N:1]([CH2:4][C:5]3[CH:14]=[C:13]4[C:8]([C:9]([C:16]5[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=5)=[CH:10][C:11](=[O:15])[O:12]4)=[CH:7][CH:6]=3)[CH:35]=2)([C:36]([F:37])([F:38])[F:39])[CH2:40][CH3:41])=[O:31])=[CH:42][CH:43]=1)([O-:25])=[O:24]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 597748703-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoateHCID 597748747-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

생성물 1

HCID 86621965(S)-1-(1-{[4-(3-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one (30 mg, 0.1 mmol) and 1-ethyl-1-(trifluoromethyl)prop-2-yn-1-yl 4-nitrobenzoate (S-isomer, the second, slower eluting enantiomer from step 2) (27 mg, 0.1 mmol) in THF (5 mL) N,N-diisopropylethylamine (79 uL, 0.45 mmol) and copper iodide (26 mg, 0.14 mmol) were added. After overnight stirring, the reaction was diluted with ethyl acetate, filtered and washed with water and brine. The organic layer was then dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (acetone/CH2Cl2 5:95) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.5 (s, 1H), 8.42 (d, 2H), 8.31 (d, 2H), 7.7-7.6 (m, 1H), 7.51 (d, 1H), 7.4-7.25 (m, 5H), 6.42 (s, 1H), 5.89 (s, 2H), 3.1-2.98 (m, 1H), 2.91-2.8 (m, 1H), 1.14 (t, 3H).

후처리

  1. filtrationfiltered
  2. washwashed with water and brine
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. customwas purified by column chromatography (acetone/CH2Cl2 5:95)

출처 및 근거

ORD 기록
ord-e14cabe28a86496e80c40cfe2658bb63
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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