Potassium Hydroxide → HCID 18470773, compound

HRID 2228612Notes

Reaction equation

HRID 2228612 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7](Br)[N:6]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]=1[CH3:19])(=[O:3])[CH3:2].C(B(CC)[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)C.[OH-].[K+]>C1(C)C=CC=CC=1.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]([C:4]1[C:8]([CH3:9])=[C:7]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[N:6]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]=1[CH3:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 133188714-(Diethylboranyl)pyridineHCID 18470728HCID 18470728, compound

Product 1

HCID 18470773HCID 18470773, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-acetyl-5-bromo-2,4-dimethyl-1-{2-(trimethylsilyl)ethoxymethyl}-1H-pyrrole (309 mg, 0.85 mmol) in toluene (5 mL) was added diethyl(4-pyridyl)borane [prepared according to the method of M. Terashima et al., Heterocycles, 1984, 22, 2471] (250 mg, 1.70 mmol), potassium hydroxide (85% purity, 168 mg, 2.55 mmol), and tetrakis(triphenylphosphine)palladium (0) (100 mg, 0.085 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 3 hours. After cooling, volatiles were removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:1) to give the title product (105 mg, 36% yield).

Workup

  1. customprepared
  2. customat room temperature
  3. temperatureThe mixture was heated
  4. temperatureat reflux temperature for 3 hours
  5. temperatureAfter cooling
  6. customvolatiles were removed by evaporation
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-eb356ae646c844d08ebd6ce3b85aedba
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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