Triphenylphosphine → Ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate

HRID 513202ノート

反応式

HRID 513202 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[F:16][C:17]([F:30])([F:29])[O:18][C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]O)=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:25][CH2:24][O:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:17]([F:16])([F:29])[F:30])=[CH:28][CH:27]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 259091Ethyl 5-Bromoindole-2-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 211086172-[4-(Trifluoromethoxy)phenoxy]ethanol

生成物 1

HCID 71212593Ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate収率 53.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of ethyl 5-bromo-1H-indole-2-carboxylate (1.7 g, 6.3 mmol), 2-[4-(trifluoromethoxy)phenoxy]ethanol (1.7 g, 7.6 mmol) and triphenylphosphine (3.3 g, 12.7 mmol) in toluene (20 ml) was added DIAD (1.85 ml, 9.5 mmol) dropwise at 0° C. The mixture was left to warm up to RT and stirred overnight. The mixture was then concentrated in vacuo. The residue was purified on silica gel (0-20% EtOAc in hexanes) to yield the title product (1.6 g).

後処理

  1. waitThe mixture was left
  2. concentrationThe mixture was then concentrated in vacuo
  3. customThe residue was purified on silica gel (0-20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-8d0f983731fd41b9bce3314c0501cbf9
出典データセット
uspto-grants-2015_08
特許番号
US09102673B2

反応ノート

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