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 513203노트

반응식

HRID 513203 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bbd470b1e6e84acd91a0a14a986e1657
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102673B2

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