HCID 59129384, compound → HCID 59129495, compound

HRID 1908452Notes

Reaction equation

HRID 1908452 reaction equation
C([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[C:16]#[C:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])(=O)CCC>C(#N)C>[CH3:23][C:18]([C:17]1[NH:6][C:7]2[C:8]([CH:16]=1)=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)([CH3:24])[C:19]([O:21][CH3:22])=[O:20]

Participants

3

Reactant 1

HCID 59129384HCID 59129384, compound

Product 1

HCID 59129495HCID 59129495, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a deoxygenated solution of methyl 4-(2-butyramido-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (1.8 g, 5.4 mmol) in acetonitrile (30 mL) was added Pd(CH3CN)2Cl2 (0.42 g, 1.6=mmol) under N2. The mixture was heated at reflux for 24 h. After cooling the mixture to ambient temperature, the solid was filtered off and washed with EtOAc (50 mL×3). The filtrate was evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=30/1) to give methyl 2-methyl-2-(5-nitro-1H-indol-2-yl)propanoate (320 mg, 23%). 1H NMR (400 MHz, CDCl3) δ 9.05 (brs, 1H), 8.52 (d, J=2.0 Hz, 1H), 8.09 (dd, J=2.0, 8.8 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 6.54 (d, J=1.6 Hz, 1H), 3.78 (d, J=9.6 Hz, 3H), 1.70 (s, 6H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. filtrationthe solid was filtered off
  4. washwashed with EtOAc (50 mL×3)
  5. customThe filtrate was evaporated under reduced pressure
  6. customto give a residue, which
  7. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate=30/1)

Sources & evidence

ORD record
ord-bb75a0a8fc44402e94b98695050150b7
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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