Tetrahydrofuran → Ethyl 2-[7-amino-1-(methoxymethyl)-1H-indol-2-yl]-1,3-thiazole-5-carboxylate

HRID 1851375Notes

Reaction equation

HRID 1851375 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:13]([O-])=O)[CH:6]=[C:5]1[C:16]1[S:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:20]=1.O1CCCC1.O.NN>O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.C(O)C>[NH2:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[N:4]([CH2:3][O:2][CH3:1])[C:5]([C:16]1[S:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:20]=1)=[CH:6]2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 57901708ethyl 2-[1-(methoxymethyl)-7-nitro-1H-indol-2-yl]-1,3-thiazole-5-carboxylate

Product 1

HCID 57901657Ethyl 2-[7-amino-1-(methoxymethyl)-1H-indol-2-yl]-1,3-thiazole-5-carboxylateYield 97.4%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-[1-(methoxymethyl)-7-nitro-1H-indol-2-yl]-1,3-thiazole-5-carboxylate (2.44 g), iron(III) chloride hexahydrate (92 mg), activated carbon (1.0 g), tetrahydrofuran (10 mL) and ethanol (5 mL) was heated under reflux for 20 min. To the reaction mixture was added hydrazine monohydrate (2.05 g) over 15 min while heating under reflux. The reaction mixture was heated under reflux for 5 hr, filtrated, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated brine, dried (MgSO4), and concentrated. Isopropyl ether was added to the obtained residue. The resulting crystals were collected by filtration, washed with isopropyl ether, and dried to give the title compound (2.18 g, yield 97%) as yellow crystals. melting point 188-190° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 min
  3. temperaturewhile heating
  4. temperatureunder reflux
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for 5 hr
  7. filtrationfiltrated
  8. concentrationthe filtrate was concentrated
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washwashed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. additionIsopropyl ether was added to the obtained residue
  14. filtrationThe resulting crystals were collected by filtration
  15. washwashed with isopropyl ether
  16. customdried

Sources & evidence

ORD record
ord-aef80e8d3dbb4cb8a704688f7842e39f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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