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Water → tert-Butyl 4-(1H-indazol-5-yl)piperazine-1-carboxylate

HRID 1192319
Notes
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Reaction equation

HRID 1192319 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[CH:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:18]([O:22][C:23](=O)[O-:24])([CH3:21])([CH3:20])[CH3:19].O>O1CCOCC1>[C:18]([O:22][C:23]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[CH:10]3)[CH2:2][CH2:3]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4613278tert-Butyl carbonateHCID 229338425-(Piperazin-1-yl)-1H-indazole

Product 1

HCID 67538337tert-Butyl 4-(1H-indazol-5-yl)piperazine-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-Piperazin-1-yl-1H-indazole (0.34 g, 1.3 mmol) in 1,4-dioxane (5 mL) was added 3N NaOH (0.42 mL, 1.3 mmol). After cooling to 0° C., a solution of tert-butylcarbonate (0.25 g, 1.3 mmol) in 1,4-dioxane (1 mL) was added dropwise. The reaction mixture was stirred at room temperature overnight and then poured into water and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3, water, brine, dried and concentrated. The residue was purified by column chromatography (EtOAc:hexanes, 1:1) to give 4-(1H-Indazol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.31 g, 82%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 10.01 (s, 1H), 7.80 (s, 1H), 7.42 (d, J=9.2 Hz, 1H), 7.21 (dd, J=9.2 Hz, J=2.0 Hz, 1H), 7.16 (d, J=2.0 Hz, 1H), 3.62 (m, 4H), 3.09 (m, 4H), 1.50 (s, 9H). LCMS (APCI+) m/z 303 [M+H]+; Rt=2.50 minutes.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3, water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (EtOAc:hexanes, 1:1)

Sources & evidence

ORD record
ord-8114f7303ccd4baca77d182d7c151228
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680114B2

Reaction notes

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