HCID 16228413, compound → HCID 10291517, compound

HRID 983915Notes

Reaction equation

HRID 983915 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2C(O)=O)=O)=[CH:3][CH:2]=1.Br[C:18](=[CH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(OC(=O)C)(=O)C>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:10]3[N:9]([C:7]=2[C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:13][CH2:12][CH2:11]3)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 16228413HCID 16228413, compoundHCID 73413130HCID 73413130, compound

Product 1

HCID 10291517HCID 10291517, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-(pyridine-4-carbonyl)pyrrolidine-2-carboxylic acid (example 19A, b; 60%, 1.5 g, 4.1 mmol), ethyl 2-bromo-3-(4-fluorophenyl)propenoate (example 19A, c; 1.0 g, 4 mmol) and acetic anhydride (10 ml) are heated under reflux for 21 h in an oil bath maintained at a temperature of 150° C. After cooling and concentrating in vacuo (Rotavapor), needles deposit. The concentrated crystal suspension is treated with ether/ethyl acetate (1:2) and the crystals are filtered off with suction. The mother liquor is completely concentrated and the residue is purified by cc (Al2O3— ether/THF 9:1):

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 21 h in an oil bath
  3. temperatureAfter cooling
  4. concentrationconcentrating in vacuo (Rotavapor), needles deposit
  5. additionThe concentrated crystal suspension is treated with ether/ethyl acetate (1:2)
  6. filtrationthe crystals are filtered off with suction
  7. concentrationThe mother liquor is completely concentrated
  8. customthe residue is purified by cc (Al2O3— ether/THF 9:1)

Sources & evidence

ORD record
ord-df8658f25b9044ffa192258aa7adea52
Source dataset
uspto-grants-2005_03
Patent number
US06867211B2

Reaction notes

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