HCID 23092682, compound → HCID 178481495, compound

HRID 2235397Notes

Reaction equation

HRID 2235397 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][C:20]=2[N+:21]([O-])=O)[N:17]([CH3:24])[C:16](=[O:25])[C:15]3([CH3:27])[CH3:26])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Fe]>[CH3:24][N:17]1[C:18]2[CH:19]=[C:20]3[NH:21][C:9]([CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:11][C:12]3=[CH:13][C:14]=2[C:15]([CH3:27])([CH3:26])[C:16]1=[O:25]

Participants

4

Reactant 1

HCID 23092682HCID 23092682, compound

Product 1

HCID 178481495HCID 178481495, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3-phenyl-N-(1,3,3-trimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-propionamide (125 mg; 248 μmol) in acetic acid (3 ml) is added iron powder (403 mg; 7 mmol). The mixture is heated and irradiated in a microwave apparatus (150° C.; 900 s). After re-cooling the mixture is filtered and evaporated. The residue is taken-up in water (40 ml) and saturated K2CO3 solution (10 ml) and extracted with CH2Cl2 (4×50 ml). The combined organic layer is dried over MgSO4 and concentrated in vacuo. The desired compound (55.0 mg) is obtained by preparative RP-HPLC eluting with a water/MeCN gradient.

Workup

  1. temperatureThe mixture is heated
  2. customirradiated in a microwave apparatus (150° C.; 900 s)
  3. temperatureAfter re-cooling the mixture
  4. filtrationis filtered
  5. customevaporated
  6. extractionsaturated K2CO3 solution (10 ml) and extracted with CH2Cl2 (4×50 ml)
  7. dry with materialThe combined organic layer is dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f18ee065625442e803c09ebd8128cf4
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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