Sodium Hydroxide → HCID 22561717, compound

HRID 1839597Notes

Reaction equation

HRID 1839597 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)O1.Br[C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[O:23][CH2:24][CH2:25][OH:26].[OH-].[Na+]>C1COCC1.[Pd].C(OCC)(=O)C>[NH:13]1[C:14]2[C:10](=[C:9]([C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[O:23][CH2:24][CH2:25][OH:26])[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 105367272-(3-BroMo-phenoxy)-ethanolHCID 113224711H-Indole-4-boronic acid, pinacol ester

Product 1

HCID 22561717HCID 22561717, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 4-(4,4,5 ,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (5.49 g, 22.5 mmol) and 2-(3-bromo-phenoxy)-ethanol (4.9 g, 22.5 mmol) in THF (68 mL) was added Palladium catalyst Pd(PPh3)4 (473 mg, 0.03 eq.) and the freshly prepared sodium hydroxide solution (2.7 g in 31.5 mL of water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 70° C. oil bath for overnight. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed with brine (4×), and dried over Na2SO4 and concentrated. The residue was purified on a silica gel column to give 5.4 g (95%) of 2-[3-(1H-indol-4-yl)-phenoxy]-ethanol.

Workup

  1. customThe system was degassed
  2. additioncharged with nitrogen
  3. customthe completion of the coupling reaction
  4. temperatureThe mixture was cooled to room temperature
  5. customseparated from water layer
  6. washThe ethyl acetate solution was washed with brine (4×)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-a67492a3b3984d7c89aeb8cebff67760
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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