Water → HCID 70818258, compound

HRID 591055Notes

Reaction equation

HRID 591055 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O.I[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:15]([O:19][CH:20]([C:26]1[C:30](B2OC(C)(C)C(C)(C)O2)=[C:29]([CH3:40])[S:28][C:27]=1[CH3:41])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:15]([O:19][CH:20]([C:26]1[C:30]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:29]([CH3:40])[S:28][C:27]=1[CH3:41])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 70818507HCID 70818507, compound

Product 1

HCID 70818258HCID 70818258, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under argon atmosphere, sodium carbonate (18 mg, 0.169 mmol), water (1.1 mL) and iodobenzene (19 μL, 0.17 mmol) were added to a solution of ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (70 mg, 0.16 mmol) in N,N-dimethylformamide (3.4 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (37 mg, 0.032 mmol) was added. The mixture was heated at 100° C. for 3 hours. The mixture was then cooled at room temperature, water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10) to afford the desired product ethyl (28g) (42 mg, 0.121 mmol, 75%).

Workup

  1. customThe solution was degassed under argon
  2. temperatureThe mixture was then cooled at room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-b0fb9884d5d946d3aa859016ef81b95e
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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