Piperidine → (Z)-1,3-Dihydro4-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

HRID 1859068Notes

Reaction equation

HRID 1859068 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:14])[NH:6]2.N1CCCCC1.[CH3:21][O:22][C:23]1[CH:27]=[CH:26][NH:25][C:24]=1[CH:28]=O.C(OCC)(=O)C>CC(O)C.O>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:28]/[C:24]1[NH:25][CH:26]=[CH:27][C:23]=1[O:22][CH3:21])/[C:5](=[O:14])[NH:6]2

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 112864661H-Pyrrole-2-carboxaldehyde, 3-methoxy-HCID 155126004-Fluoro-5-nitroindolin-2-one2×

Product 1

HCID 15512601(Z)-1,3-Dihydro4-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

1,3-Dihydro-4-fluoro-5-nitro-2H-indol-2-one (5.25 g, 26.8 mmol) (Starting Material 9) was suspended in 110 mL solution of 1.35% piperidine in 2-propanol (Aldrich). 3-Methoxy-2-pyrrolecarboxaldehyde (3.68 g, 29.4 mmol, 1.1 eq.)(Bellamy, supra) was added and this mixture heated at 60° C. for 3.5 hours (TLC: 50% ethyl acetate in hexanes). The reaction mixture was poured into 1 L ice and water mixture and the solid precipitate filtered, washed with water and dried at 50° C. under high vacuum to give (Z)-1,3-dihydro-4-fluoro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-nitro-2H-indol-2-one as an orange-brown solid. (Yield 6.6 g, 81%).

Workup

  1. filtrationthe solid precipitate filtered
  2. washwashed with water
  3. customdried at 50° C. under high vacuum

Sources & evidence

ORD record
ord-acf5040a3ee5452db029b08e7146b024
Source dataset
uspto-grants-2000_11
Patent number
US06153634

Reaction notes

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