| Identification | Back Directory | [Name]
tert-Butyl 4-iodopyrazole-1-carboxylate | [CAS]
121669-70-3 | [Synonyms]
1-BOC-4-IODOPYRAZOLE
1-Boc-4-iodopyrazole 95%
t-Butyl4-iodopyrazole-1-carboxylate
TERT-BUTYL 4-IODOPYRAZOLE-1-CARBOXYLATE
T-BUTYL 4-IODO-1H-PYRAZOLE-1-CARBOXYLATE
tert-Butyl-4-iodo-1H-pyrazole-1-carboxylate
3-tert-butyl-4-iodo-1H-pyrazole-1-carboxylate
4-iodo-1-pyrazolecarboxylic acid tert-butyl ester
4-IODO-PYRAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
1H-Pyrazole-1-carboxylic acid, 4-iodo-, 1,1-dimethylethyl ester
1-Boc-3-Methyl-4-iodo-1H-pyrazole 1H-Pyrazole-1-carboxylic acid, 4-iodo-, 1,1-dimethylethyl ester | [Molecular Formula]
C8H11IN2O2 | [MDL Number]
MFCD05663855 | [MOL File]
121669-70-3.mol | [Molecular Weight]
294.09 |
| Chemical Properties | Back Directory | [Melting point ]
67-70°C | [Boiling point ]
312.0±34.0 °C(Predicted) | [density ]
1.70±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C(protect from light) | [pka]
-3.01±0.12(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C8H11IN2O2/c1-8(2,3)13-7(12)11-5-6(9)4-10-11/h4-5H,1-3H3 | [InChIKey]
WRCRIGRVTPLDDD-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)C=C(I)C=N1 |
| Hazard Information | Back Directory | [Synthesis]
At room temperature, 4-iodopyrazole (20 mmol) was dissolved in THF (60 mL) and Et3N (30 mmol) and di-tert-butyl dicarbonate (Boc) 2O (22 mmol) were added sequentially. After 2 hours of reaction, N-Boc-4-iodopyrazole (5.88 g, 100% yield) was obtained. Subsequently, N-Boc-4-iodopyrazole was dissolved in THF (100 mL) under nitrogen protection, Pd(Ph3P)4 (1.1 g, 1 mmol) and hexamethyldistannane (20 mmol) were added, and the reaction was carried out at 78 °C overnight. After completion of the reaction, 10% KF aqueous solution was added, stirred for 30 min and filtered through a diatomaceous earth pad. The filtrate was extracted with EtOAc, the organic layer was washed with water and dried over MgSO4. After filtration and concentration, it was purified by column chromatography to give 3-trimethylstannopyrazole derivative (5 g, 75% yield) as a white solid. | [References]
[1] Patent: EP946508, 2009, B1. Location in patent: Page/Page column 58
[2] Patent: WO2012/123745, 2012, A1. Location in patent: Page/Page column 64
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 32, p. 8290 - 8294
[4] Angew. Chem., 2013, vol. 125, # 32, p. 8448 - 8452,5
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 10045 - 10065 |
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