Tetrahydrofuran → 1-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indole-7-amine

HRID 1851370Notes

Reaction equation

HRID 1851370 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][CH:18]=[CH:19][N:20]=1.O1CCCC1.O.NN>O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.CO>[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH2:13])[CH:6]=[C:5]1[C:16]1[S:17][CH:18]=[CH:19][N:20]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 579018301-(Methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole

Product 1

HCID 579017321-(Methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indole-7-amineYield 97.5%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole (2.14 g), iron(III) chloride hexahydrate (0.12 g), activated carbon (1.20 g), tetrahydrofuran (10 mL) and methanol (10 mL) was heated under reflux for 20 min. To the reaction mixture was added hydrazine monohydrate (2.20 g) over 15 min while heating under reflux. The reaction mixture was heated under reflux for 2 hr, filtrated, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (1.87 g, yield 97%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

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 2 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

Sources & evidence

ORD record
ord-74d40bdc0da041a1aedc65aa07ebaecf
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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