Methyl 4-chloroacetoacetate → HCID 178498741, compound

HRID 402628Notes

Reaction equation

HRID 402628 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][CH2:11][C:12](=[O:18])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.ClCC(=O)CC(OC)=O.FC1C=CC(N=C=O)=CC=1.[NH:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][N:45]=2)[C:40]([CH:47]=O)=[CH:39]1.N1CCC[C@H]1C(O)=O>CC(O)C>[NH:38]1[C:46]2=[N:45][CH:44]=[CH:43][CH:42]=[C:41]2[C:40]([CH:47]=[C:11]2[O:10][C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:12]2=[O:18])=[CH:39]1

Participants

7

Reactant 5

HCID 36240Methyl 4-chloroacetoacetateHCID 709554-Fluorophenyl isocyanateHCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708321HCID 86708321, compound

Product 1

HCID 178498741HCID 178498741, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of methyl 2-[(4-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.25 g, 1.0 mmol) which similarly prepared according to the procedure described in the Example 2, First step using methyl 4-chloroacetoacetate and 4-fluorophenyl isocyanate, and 7-azaindole-3-carboxaldehyde (0.15 g, 1.0 mmol) in 2-propanol (5.0 mL), L-proline (0.023 g, 0.20 mmol) was added at ambient temperature. The mixture was refluxed for 2 days. Cooled to ambient temperature, the precipitate was collected by filtration, washed with ethanol and diisopropyl ether then dried to afford the titled compound as solid (0.26 g, y. 68%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 2 days
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethanol and diisopropyl ether
  5. customthen dried

Sources & evidence

ORD record
ord-92a379be05fb4535a8a9b2b4b1fd662f
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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