Sodium Carbonate → HCID 66743556, compound

HRID 1893242Notes

Reaction equation

HRID 1893242 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH:10]=2)O1.Br[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]#[N:29])=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:13]1[C:12]2([CH2:17][CH2:18][C:9]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]#[N:29])=[CH:23][CH:22]=3)=[CH:10][CH2:11]2)[O:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27914Benzeneacetonitrile, 4-bromo-HCID 36970768-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro(4.5)dec-7-ene

Product 1

HCID 66743556HCID 66743556, compound

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene (as prepared by PCT Int. Appl. WO2006064189, 1.81 g, 6.80 mmol), 4-bromo-phenyl-acetonitrile (Aldrich, 1.40 g, 7.10 mmol), and tetrakis(triphenylphosphino)-palladium(0) (Aldrich, 350 mg, 0.34 mmol) in 1,4-dioxane (20 mL), was treated with 2M aqueous Na2CO3 (7 mL, 14.0 mmol), bubbled with argon for a few minutes, and heated to 100° C. under reflux condenser for 24 h. After cooling to ambient temperature, the reaction was diluted with water (30 mL) and extracted thrice with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate concentrated in vacuo to give a colorless oil. Purification by silica gel column, using a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate), afforded the title compound as a white solid.

Workup

  1. custombubbled with argon for a few minutes
  2. temperatureunder reflux condenser for 24 h
  3. temperatureAfter cooling to ambient temperature
  4. additionthe reaction was diluted with water (30 mL)
  5. extractionextracted thrice with dichloromethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo
  10. customto give a colorless oil
  11. customPurification by silica gel column

Sources & evidence

ORD record
ord-5318e4f20e8d41f6b397d79e1c9c5f72
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

Loading…