Toluene → HCID 178424432, compound

HRID 2299262Notes

Reaction equation

HRID 2299262 reaction equation
[NH2:1][C:2]1[C:3]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])=[C:4]2[N:9]([C:10]=1[C:11](OCC)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5]2.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:35]1(C)[CH:40]=CC=C[CH:36]=1>COC(OC)(C)C>[OH:12][C:11]1[C:10]2[N:9]3[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]3)=[C:3]([C:16]3[C:17]([CH3:24])=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=3[CH3:22])[C:2]=2[N:1]=[C:35]([CH3:40])[CH:36]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22034120HCID 22034120, compound

Product 1

HCID 178424432HCID 178424432, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

To a solution of 2-amino-3-ethoxycarbonyl-1-(2,4,6-trimethylphenyl)-indolizine (19.2 g; 59.6 mmol) in 2,2-dimethoxypropane (100 mL) is added di-camphorsulfonic acid (0.2 g). The mixture is stirred at reflux for 30 minutes and then distilled slowly to remove ca. 60 mL of volatiles over a 30-minute period. The solution is cooled to ambient temperature under an inert atmosphere, diluted with anhydrous toluene (50 mL), and concentrated in vacuo. The residue is dissolved in toluene (50 mL) and to the stirred solution is then added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (250 mL; 125 mmol) dropwise over a 1-hour period. After the addition is complete, the mixture is further stirred for 2 hours at room temperature before being concentrated in vacuo to a small volume and then diluted with aqueous ammonium chloride. The resulting emulsion-like biphasic mixture is suction-filtered and washed succesively with water, methanol, and ethyl ether. Air- and vacuum drying provides 10.1 g of the title compound as a pale yellow solid (54%).

Workup

  1. temperatureat reflux for 30 minutes
  2. distillationdistilled slowly
  3. customto remove ca. 60 mL of volatiles over a 30-minute period
  4. additiondiluted with anhydrous toluene (50 mL)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in toluene (50 mL) and to the stirred solution
  7. additionAfter the addition
  8. stirringthe mixture is further stirred for 2 hours at room temperature
  9. concentrationbefore being concentrated in vacuo to a small volume
  10. additiondiluted with aqueous ammonium chloride
  11. filtrationThe resulting emulsion-like biphasic mixture is suction-filtered
  12. washwashed succesively with water, methanol, and ethyl ether
  13. customAir- and vacuum drying

Sources & evidence

ORD record
ord-8674363f345c4885859d52987c9040ce
Source dataset
uspto-grants-2002_12
Patent number
US06495686B2

Reaction notes

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