HCID 58926231, compound → HCID 58926066, compound

HRID 333359Notes

Reaction equation

HRID 333359 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12]3/[CH:13]=[C:14]([C:17]4[N:18](C(OC(C)(C)C)=O)[CH:19]=[CH:20][CH:21]=4)[CH2:15][O:16]/3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12]3\[O:16][CH2:15][C:14]([C:17]4[NH:18][CH:19]=[CH:20][CH:21]=4)=[CH:13]\3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58926231HCID 58926231, compound

Product 1

HCID 58926066HCID 58926066, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-[(5E)-5-(6-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2,5-dihydrofuran-3-yl]-1H-pyrrole-1-carboxylate (Example 37; 30 mg) in a mixture of trifluoroacetic acid (2 mL) and CH2Cl2 (10 mL) was stirred at room temperature for 16 hours. The mixture was evaporated to dryness, and re-dissolved in 1:1 THF/MeOH (4 mL). The solution was slowly added into diluted NaHCO3 solution (100 mL) with stirring. The precipitates were filtered, washed with water, and dried in vacuum to give (3E)-6-fluoro-3-[4-(1H-pyrrol-2-yl)furan-2(5H)-ylidene]-1,3-dihydro-2H-indol-2-one as brown solid. Yield: 15 mg.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionre-dissolved in 1:1 THF/MeOH (4 mL)
  3. additionThe solution was slowly added into diluted NaHCO3 solution (100 mL)
  4. stirringwith stirring
  5. filtrationThe precipitates were filtered
  6. washwashed with water
  7. customdried in vacuum

Sources & evidence

ORD record
ord-f52eaabce1e8421d81522198bb661b83
Source dataset
uspto-grants-2014_11
Patent number
US08877923B2

Reaction notes

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