Ethanol → HCID 53978622, compound

HRID 1604677Notes

Reaction equation

HRID 1604677 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]([N:21]4[C:29]5[C:24](=[CH:25][C:26]([N+:30]([O-])=O)=[CH:27][CH:28]=5)[C:23]([CH2:33][C:34]([O:36][CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[O:35])=[CH:22]4)=[O:20])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:30][C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[N:21]([C:19]([C:16]1[CH:17]=[CH:18][C:12]3[O:11][C:10]([C:7]4[S:8][CH:9]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[N:6]=4)=[CH:14][C:13]=3[CH:15]=1)=[O:20])[CH:22]=[C:23]2[CH2:33][C:34]([O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:35]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 19603752HCID 19603752, compound

Product 1

HCID 53978622HCID 53978622, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}-5-nitroindol-3-acetate (450 mg), iron powders (450 mg) and ammonium chloride (45 mg) in a mixed solvent of ethanol (7 ml) and water (3 ml) was stirred under reflux for 1 hour. After being cooled to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give benzyl 5-amino-1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]carbonyl}indole-3-acetate (259 mg).

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washeluted with a mixture of toluene and ethyl acetate
  5. additionThe fractions containing the objective compound
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f07b490d72db49a19eecdf21857c63ac
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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