N,N,N',N'-Tetramethylazodicarboxamide → {6-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

HRID 890436노트

반응식

HRID 890436 반응식
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][C:20]1[C:25]([CH2:26]O)=[CH:24][CH:23]=[C:22]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[N:21]=1.C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>O1CCCC1>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:26][C:25]3[C:20]([CH3:19])=[N:21][C:22]([C:28]4[CH:29]=[CH:30][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:32][CH:33]=4)=[CH:23][CH:24]=3)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 21935862[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanolHCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

생성물 1

HCID 69642195{6-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice cold solution of (6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (70 mg, 0.28 mmol), [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (76 mg, 0.28 mmol) and tributylphosphine (110 μl, 0.42 mmol) in tetrahydrofuran (4 ml) was added N,N,N′,N′-tetramethyl azodicarboxamide (73 mg, 0.42 mmol) under an argon atmosphere. The cooling bath was removed and stirring continued for 14 h. Filtration over celite and evaporation of the solvent under reduced pressure gave a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to give 105 mg (0.21 mmol, 75%) of the title compound as white crystals.

후처리

  1. customThe cooling bath was removed
  2. filtrationFiltration
  3. customover celite and evaporation of the solvent under reduced pressure
  4. customgave a yellow oil which
  5. customwas purified by column chromatography (silica gel, heptane/AcOEt)

출처 및 근거

ORD 기록
ord-1b1af166a4f74348ad6e91f9c0ea8997
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995263B2

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