N,N,N',N'-Tetramethylazodicarboxamide → {6-[2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

HRID 915395노트

반응식

HRID 915395 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].[CH3:17][N:18]1[C:22]([CH2:23]O)=[CH:21][C:20]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[N:19]1.C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:23][C:22]3[N:18]([CH3:17])[N:19]=[C:20]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:29][CH:30]=4)[CH:21]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

참가 물질

6

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 44818671(1-Methyl-3-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-YL)methanolHCID 68821422(6-Hydroxy-indol-1-yl)-acetic acid ethyl ester

생성물 1

HCID 69280222{6-[2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester수율 30%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice cold solution of (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (35 mg, 160 μmol; example 2 e]), [2-methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-methanol (41 mg, 160 μmol) and tributylphosphine (50 μl, 19 μmol) in tetrahydrofuran (3.5 ml) was added N,N,N′,N′-tetramethyl azodicarboxamide (33 mg, 19 μmol). The cooling bath was removed and stirring continued for 14 h. The mixture was filtered over celite and the solvent removed under reduced pressure to give a brown oil which was purified by column chromatography (silica gel, heptane/AcOEt) to obtain 22 mg (50 μmol, 30%) of the title compound as colorless oil.

후처리

  1. customThe cooling bath was removed
  2. filtrationThe mixture was filtered over celite
  3. customthe solvent removed under reduced pressure
  4. customto give a brown oil which
  5. customwas purified by column chromatography (silica gel, heptane/AcOEt)

출처 및 근거

ORD 기록
ord-d405da9e03344094b778b02662927e74
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265149B2

반응 노트

불러오는 중…