Aluminum(III) Chloride → 4-(benzyloxy)-1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indole

HRID 1404132노트

반응식

HRID 1404132 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[Cl-].[Cl-].[Al+3].[CH2:11]([O:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]2[C:20]=1[C:21]([CH2:31][C:32]([N:34]1[CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35]1)=O)=[CH:22][N:23]2[CH2:29][CH3:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([O:18][C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]2[C:20]=1[C:21]([CH2:31][CH2:32][N:34]1[CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:42]1)=[CH:22][N:23]2[CH2:29][CH3:30])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 672350282-(4-(benzyloxy)-1-ethyl-6-fluoro-1H-indol-3-yl)-1-(isoindolin-2-yl)ethanone

생성물 1

HCID 509963494-(benzyloxy)-1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indole수율 57.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of LiAlH4 (100 mg, 2.6 mmol) in THF (30 mL) was added aluminum trichloride (463 mg, 3.51 mmol) at 0° C. After stirring for 10 min, a solution of 31-2 (180 mg, 0.42 mmol) in THF (5 mL) was added dropwise. The reaction mixture was stirred for 5 min before Na2SO4.10H2O was added to quench the reaction. The solid was filtered off and the filtrate was evaporated. The resulting residue was purified on silica gel column chromatography eluting with dichloromethane/methanol (10:1) to get 31-3 (100 mg, 57%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.46 (d, J=7.2 Hz, 2H), 7.31-7.26 (m, 4H), 7.27 (t, J=3.6 Hz, 1H), 7.09-7.06 (m, 2H), 6.93 (s, 1H), 6.65 (d, J=7.2 Hz, 1H), 6.42 (d, J=7.2 Hz, 1H), 5.06 (s, 2H), 4.02-4.00 (m, 6H), 3.27 (s, 4H), 1.41 (t, J=7.4 Hz, 3H). LRMS: calc 414.2 and found: 414.9 [M+1].

후처리

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. filtrationThe solid was filtered off
  5. customthe filtrate was evaporated
  6. customThe resulting residue was purified on silica gel column chromatography
  7. washeluting with dichloromethane/methanol (10:1)

출처 및 근거

ORD 기록
ord-998fd6208eeb4d178cfd2370d2e38aa9
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912220B2

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