Tetrahydrofuran → ethyl 1-(2-aminoethyl)-1H-indazole-5-carboxylate

HRID 1007675Notes

Reaction equation

HRID 1007675 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[N:15]1.NN.C1COCC1>C(O)C.C1COCC1>[NH2:3][CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 10832532Ethyl 1-[2-(1,3-dioxoisoindolin-2-yl)ethyl]-1H-indazole-5-carboxylate

Product 1

HCID 10585718ethyl 1-(2-aminoethyl)-1H-indazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Ethyl 1-[2-(1,3-dioxoisoindolin-2-yl)ethyl]-1H-indazole-5-carboxylate (step A, 980 mg, 2.7 mmol) was dissolved in ethanol/THF (1:1, 35 mL) under nitrogen. Hydrazine (365 uL) was added and the reaction stirred 17 hours. THF (75 mL) was added and the resulting solids were filtered off. The filtrate was concentrated to an orange solid, which was purified by flash chromatography (dichoromethane/5% methanol/0.5% triethylamine). The product fractions were combined and concentrated to an orange solid (404 mg, 66%). LRMS (ES): 234.1 ([M+H]+, 100%)

Workup

  1. filtrationthe resulting solids were filtered off
  2. concentrationThe filtrate was concentrated to an orange solid, which
  3. customwas purified by flash chromatography (dichoromethane/5% methanol/0.5% triethylamine)
  4. concentrationconcentrated to an orange solid (404 mg, 66%)

Sources & evidence

ORD record
ord-930dc22d46cb4a0998765fee7b36e863
Source dataset
uspto-grants-2004_09
Patent number
US06794518B1

Reaction notes

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