Potassium Acetate → Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate

HRID 513203ノート

反応式

HRID 513203 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:5]2.[BH3:30].[OH:31][C:32]([C:35]([OH:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].CC([O-])=O.[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:33][C:32]1([CH3:34])[C:35]([CH3:37])([CH3:36])[O:38][B:30]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)[C:6]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:5]3)[O:31]1

参加物

6

反応物 3

HCID 517044Potassium AcetateHCID 71212593Ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylateHCID 178419189HCID 178419189、化合物

生成物 1

HCID 71212616Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate収率 76.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

The ethyl 5-bromo-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-indole-2-carboxylate (812 mg, 1.7 mmol), pinacol borane (873 mg, 3.4 mmol), X Phos (98 mg, 0.21 mmol) and KOAc (540 mg, 5.5 mmol) were combined in 8 mL of Dioxane. The mixture was degassed under vacuum and backfilled with N2. Palladium acetate (23 mg, 0.1 mmol) was added, and the mixture was degassed and back filled again. The mixture was left to stir overnight at 85° C. EtOAc was added and the mixture was filtered through a pad of celite, concentrated in vacuo, and purified on silica (0-30% EtOAc in hexanes) to give the title product (675 mg).

後処理

  1. customThe mixture was degassed under vacuum
  2. customthe mixture was degassed
  3. additionback filled again
  4. waitThe mixture was left
  5. additionEtOAc was added
  6. filtrationthe mixture was filtered through a pad of celite
  7. concentrationconcentrated in vacuo
  8. custompurified on silica (0-30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-bbd470b1e6e84acd91a0a14a986e1657
出典データセット
uspto-grants-2015_08
特許番号
US09102673B2

反応ノート

読み込み中…