4-Fluorophenol → 9-[1-(3,4-Dimethoxybenzoyl)-2-[5-(4-fluorophenoxy)pentyl]-1,2,3,4-tetrahydro-4-quinolinyl]-9H-carbazole

HRID 585394

반응식

HRID 585394 반응식
[CH:1]1[C:13]2[N:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:24](=[O:35])[C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)[CH:16]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41])[CH2:15]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[F:42][C:43]1[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[O:31][CH3:32])[C:24]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]([N:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:15][CH:16]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][O:41][C:46]1[CH:47]=[CH:48][C:43]([F:42])=[CH:44][CH:45]=1)=[O:35]

참가 물질

6

반응물 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 223392335-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-1-pentanol

생성물 1

HCID 223392989-[1-(3,4-Dimethoxybenzoyl)-2-[5-(4-fluorophenoxy)pentyl]-1,2,3,4-tetrahydro-4-quinolinyl]-9H-carbazole수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-1-pentanol (0.12 g, 0.22 mmol) prepared in Example 135 was mixed with 4-fluorophenol (50 mg, 0.44 mmol), tetrahydrofuran (4 ml), diethyl azodicarboxylate (69 μl, 0.44 mmol) and triphenylphosphine (0.11 g, 0.44 mmol), followed by stirring overnight at room temperature. After distilling off the solvent, the residue was partitioned between ethyl acetate and water, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and then evaporated to remove the solvent. The residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/10) to give the titled compound (0.13 g, yield: 93%) as a white crystal (cis:trans=4:1).

후처리

  1. distillationAfter distilling off the solvent
  2. customthe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent

출처 및 근거

ORD 기록
ord-a1cedb0e7b554d69ba0f469493e94ad8
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930104B2

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