| Identification | Back Directory | [Name]
4-BROMO-2,3-DIHYDRO-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER | [CAS]
885272-46-8 | [Synonyms]
N-Boc-4-broMoindoline
tert-Butyl 4-broMoindoline-1-carboxylate
Tert-butyl 4-bromo-2,3-dihydroindole-1-carboxylate
4-BROMO-2,3-DIHYDRO-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
1H-Indole-1-carboxylic acid, 4-broMo-2,3-dihydro-, 1,1-diMethylethyl ester | [Molecular Formula]
C13H16BrNO2 | [MDL Number]
MFCD08059277 | [MOL File]
885272-46-8.mol | [Molecular Weight]
298.18 |
| Chemical Properties | Back Directory | [Boiling point ]
362.0±41.0 °C(Predicted) | [density ]
1.400±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
-0.34±0.20(Predicted) | [Appearance]
White to yellow Solid-Liquid Mixture | [InChI]
InChI=1S/C13H16BrNO2/c1-13(2,3)17-12(16)15-8-7-9-10(14)5-4-6-11(9)15/h4-6H,7-8H2,1-3H3 | [InChIKey]
DUZIJTYKDFFQDJ-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)C2=C(C(Br)=CC=C2)CC1 |
| Hazard Information | Back Directory | [Synthesis]
The reaction mixture was stirred overnight at room temperature in acetonitrile (8 mL) with 4-bromo-2,3-dihydro-1H-indole (759 mg, 3.81 mmol) and di-tert-butyl dicarbonate (976 mg, 4.48 mmol). After completion of the reaction, the solvent was removed by rotary evaporation and the residue was dissolved in ethyl acetate (40 mL). The organic layer was washed sequentially with water (3 x 20 mL) and saturated saline (1 x 20 mL). The organic phase was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Finally, it was purified by silica gel column chromatography (eluent: petroleum ether) to afford N-Boc-4-bromoindoline (840 mg, 74% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ 1.50 (s, 9H), 3.02 (t, J = 8.8 Hz, 2H), 3.94 (t, J = 8.8 Hz, 2H) 7.12 (m, 2H), 7.56 (m, 1H). | [References]
[1] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 225
[2] Patent: US2013/102595, 2013, A1. Location in patent: Paragraph 0566
[3] Patent: JP2015/187145, 2015, A. Location in patent: Paragraph 0481
[4] Patent: WO2016/25933, 2016, A2. Location in patent: Page/Page column 185 |
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