Sodium Carbonate → HCID 70819123, compound

HRID 591063Notes

Reaction equation

HRID 591063 reaction equation
[C:1]([O:5][CH:6]([C:12]1[C:16](B2OC(C)(C)C(C)(C)O2)=[C:15]([CH3:26])[S:14][C:13]=1[CH3:27])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S(O[C:34]1[CH:43]=[CH:42][C:41]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=2[CH:35]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([P]([Pd]([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)=CC=1>[C:1]([O:5][CH:6]([C:12]1[C:16]([C:34]2[CH:43]=[CH:42][C:41]3[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=3[CH:35]=2)=[C:15]([CH3:26])[S:14][C:13]=1[CH3:27])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 11087165HCID 11087165, compoundHCID 70818507HCID 70818507, compound

Product 1

HCID 70819123HCID 70819123, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under argon atmosphere, ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (50 mg, 0.12 mmol), 5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (39a) (41.4 mg, 0.15 mmol) and sodium carbonate (13.7 mg, 0.13 mmol) were dissolved in dimethylformamide (2.5 mL) and water (0.85 mL). The solution was degassed under argon for 10 minutes and Tetrakis(triphenylphosphine)palladium (28.5 mg, 0.02 mmol) was added. The reaction was heated and shaken at 100° C. for 4 hours. After cooling at room temperature, water was added and the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by preparative TLC (cyclohexane/ethyl acetate: 9/1) to provide the desired product (39b) (40 mg, 0.1 mmol, 77%).

Workup

  1. customThe solution was degassed under argon for 10 minutes
  2. temperatureThe reaction was heated
  3. temperatureAfter cooling at room temperature
  4. customthe mixture was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by preparative TLC (cyclohexane/ethyl acetate: 9/1)

Sources & evidence

ORD record
ord-d39ace8e0563410998e2d727b229dbc1
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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