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Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1) → Ethyl 2-(2-bromo-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-3-fluoro-2-phenyl-1H-indole-6-carbonyl)thiophen-3-yl)acetate

HRID 1952510
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HRID 1952510 반응식
[Br:1][C:2]1[S:3][C:4]([C:13]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[C:20]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:21]3[CH2:24][CH2:25][CH2:26][CH2:27][N:28]3[C:36](=[O:37])[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]3=[O:38])=[CH:17][CH:16]=2)=[O:14])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[O-]S(C(F)(F)[F:50])(=O)=O.F[N+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[Br:1][C:2]1[S:3][C:4]([C:13]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([F:50])=[C:20]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[N:21]3[CH2:24][CH2:25][CH2:26][CH2:27][N:28]3[C:36](=[O:37])[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]3=[O:38])=[CH:17][CH:16]=2)=[O:14])=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)HCID 67502223Ethyl 2-(2-bromo-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-2-phenyl-1H-indole-6-car-bonyl)thiophen-3-yl)acetate

생성물 1

HCID 67496700Ethyl 2-(2-bromo-5-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-3-fluoro-2-phenyl-1H-indole-6-carbonyl)thiophen-3-yl)acetate수율 19%

시약·촉매·용매 2

HCID 3283Diethyl Ether
용매
HCID 6344Dichloromethane용매

실험 절차

To a solution of 5 (209 mg, 0.31 mmol) in 3 mL CH2Cl2 was added 1-fluoropyridinium triflate (81 mg, 0.33 mmol), and then the mixture stirred at room temperature until no 5 was detected by NMR. The resulting mixture was diluted with 40 mL Et2O, washed with brine (2×10 mL), dried over MgSO4, filtered, and then concentrated in vacuo. MPLC purification (Hex/EtOAc 9:1) gave 6 (40 mg, 19%) as a yellow amorphous solid. 1H NMR (400 MHz, CDCl3) δ 7.94 (s, 1H), 7.77-7.63 (m, 6H), 7.57 (s, 1H), 7.48-7.40 (m, 5H), 4.25 (t, J=7.2 Hz, 2H), 4.16 (q, J=7.2 Hz, 2H), 3.72 (s, 2H), 3.48 (t, J=6.8 Hz, 2H), 1.65-1.61 (m, 2H), 1.50-1.44 (m, 2H), and 1.26 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 187.16, 169.94, 168.50, 143.96, 143.10, 140.65, 135.88, 135.17, 134.22, 134.17, 132.37, 132.31, 132.11, 131.68, 129.96, 129.51, 129.17, 129.13, 128.96, 128.45, 127.58, 127.38, 123.46, 121.80, 121.19, 120.18, 120.03, 116.97, 112.58, 61.52, 43.64, 37.21, 35.33, 27.32, 25.76, and 14.44; 19F NMR (376 MHZ, CDCl3) δ −174.33.

후처리

  1. washwashed with brine (2×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customMPLC purification (Hex/EtOAc 9:1)

출처 및 근거

ORD 기록
ord-bf44b73bfaf54f62af5d3a1a29d6f2f3
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08404728B2

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