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

HRID 751180

反応式

HRID 751180 の反応式
[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]

参加物

6

反応物 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]-

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4bc37d558c684ffb9b7c36d389bdd448
出典データセット
uspto-grants-2008_07
特許番号
US07405236B2

関連ノート

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