N,N,N',N'-Tetramethylazodicarboxamide → {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester

HRID 751180

반응식

HRID 751180 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].[F:17][C:18]([F:33])([F:32])[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][CH2:28][CH2:29][CH2:30]O)=[CH:22][CH:21]=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][CH2:30][CH2:29][CH2:28][C:27]#[C:26][C:23]3[CH:24]=[CH:25][C:20]([O:19][C:18]([F:17])([F:32])[F:33])=[CH:21][CH:22]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

참가 물질

6

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 68821422(6-Hydroxy-indol-1-yl)-acetic acid ethyl esterHCID 688226904-Pentyn-1-ol, 5-[4-(trifluoromethoxy)phenyl]-

생성물 1

HCID 68826126{6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester수율 33%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice cold solution of (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (100 mg, 455 μmol), 5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol (111 mg, 455 μmol) and tributylphosphine (160 μl, 546 μmol) in tetrahydrofuran (10 ml) was added N,N,N′,N′-tetramethyl azodicarboxamide (94 mg, 546 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 yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to obtain 65 mg (150 μmol, 32%) 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 yellow oil which
  5. customwas purified by column chromatography (silica gel, heptane/AcOEt)

출처 및 근거

ORD 기록
ord-4bc37d558c684ffb9b7c36d389bdd448
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405236B2

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