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

HRID 2252468Notes

Reaction equation

HRID 2252468 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-f0d6551c9f1d4c0382ffe7a430945bdc
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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