HCID 58926237, compound → HCID 24964166, compound

HRID 333358Notes

Reaction equation

HRID 333358 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12]3\[O:13][CH2:14][C:15]([C:17]4[CH:21]=[CH:20][N:19]([Si](C(C)C)(C(C)C)C(C)C)[CH:18]=4)=[CH: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:13][CH2:14][C:15]([C:17]4[CH:21]=[CH:20][NH:19][CH:18]=4)=[CH:16]\3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58926237HCID 58926237, compound

Product 1

HCID 24964166HCID 24964166, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (3E)-6-fluoro-3-{4-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]furan-2(5H)-ylidene}-1,3-dihydro-2H-indol-2-one (Example 33; 90 mg) in a mixture of trifluoroacetic acid (7 mL) and CH2Cl2 (7 mL) was stirred at room temperature for 3 days. The mixture was evaporated to dryness, and re-dissolved in 1:1 THF/MeOH (6 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-3-yl)furan-2(5H)-ylidene]-1,3-dihydro-2H-indol-2-one as brown solid. Yield: 40 mg.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionre-dissolved in 1:1 THF/MeOH (6 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-74c07eb12f3d4558b88aff1dd39fa1ea
Source dataset
uspto-grants-2014_11
Patent number
US08877923B2

Reaction notes

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