Triethylamine → 7-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

HRID 2114872Notes

Reaction equation

HRID 2114872 reaction equation
Cl[CH2:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[F:16])[CH3:6])=[O:4].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[F:16][C:8]1[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[C:12]2[C:7]=1[N:5]([CH3:6])[C:3](=[O:4])[CH2:2]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 119518482-chloro-N-(2-fluoro-4-nitrophenyl)-N-methylacetamide

Product 1

HCID 119516757-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Following the method described by Hennessy and Buchwald in J. Am. Chem. Soc., 2003, 125, 12084-12085, 2-chloro-N-(2-fluoro-4-nitro-phenyl)-N-methyl-acetamide (15, 1.00 g, 4.05 mol), palladium acetate (27.3 mg, 0.122 mmol) and 2-(di-tert-butylphosphino)biphenyl (72.5 mg, 0.243 mmol) are placed under a nitrogen atmosphere, and toluene (20 ml) and triethylamine (0.85 ml, 6.08 mmol) are added via syringe. The reaction is heated at 80° C. for 4 hours and then evaporated to dryness. The dark residue is purified by PTLC (dichloromethane) to give the title compound as a light brownish-orange solid. HPLC r.t. 4.4 min.

Workup

  1. customevaporated to dryness
  2. customThe dark residue is purified by PTLC (dichloromethane)

Sources & evidence

ORD record
ord-d30259fc3516408591ae7645bb8f5d36
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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