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 513203Notes

Reaction equation

HRID 513203 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bbd470b1e6e84acd91a0a14a986e1657
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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