| Identification | Back Directory | [Name]
4-BROMO-2,3-DIHYDRO-1H-INDOLE | [CAS]
86626-38-2 | [Synonyms]
4-bromoindoline
4-BROMO-2,3-DIHYDRO-1H-INDOLE
4-bromoindoline hydrochloride
1H-Indole,4-broMo-2,3-dihydro-
4-BroMo-2,3-dihydro-1H-indole 1HCl salt
4-BROMO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE
4-Bromoindoline 4-Bromo-2,3-dihydro-1H-indole in stock Factory | [Molecular Formula]
C8H8BrN | [MDL Number]
MFCD07371633 | [MOL File]
86626-38-2.mol | [Molecular Weight]
198.06 |
| Chemical Properties | Back Directory | [Boiling point ]
278.8±29.0 °C(Predicted) | [density ]
1.514±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C(protect from light) | [form ]
liquid | [pka]
4.20±0.20(Predicted) | [color ]
Brown to reddish brown | [InChI]
InChI=1S/C8H8BrN/c9-7-2-1-3-8-6(7)4-5-10-8/h1-3,10H,4-5H2 | [InChIKey]
YCJCSDSXVHEBRU-UHFFFAOYSA-N | [SMILES]
N1C2=C(C(Br)=CC=C2)CC1 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale-yellow to Yellow to Brown Liquid | [Uses]
4-Bromoindoline is a simple active pharmaceutical building block that can be used as a basic skeleton for the preparation of the migraine drug Sumatriptan. | [Synthesis]
Step 1. 4-Bromoindole (5.00 mL, 39.9 mmol) was dissolved in a solvent mixture of acetic acid (5.00 mL, 87.9 mmol) and methanol (25.0 mL, 617 mmol) and the reaction system was cooled to 0°C. Sodium cyanoborohydride (7.52 g, 0.120 mol) was slowly added under stirring, followed by a slow warming of the reaction mixture to room temperature over 1 hour. After completion of the reaction, the mixture was concentrated and neutralized with saturated aqueous sodium bicarbonate solution. Extraction was carried out using ether and ethyl acetate, the organic phases were combined and washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give 4.11 g (52% yield) of 4-bromo-2,3-dihydro-1H-indole. | [References]
[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2462 - 2471
[2] Patent: US2007/265258, 2007, A1. Location in patent: Page/Page column 24
[3] Patent: WO2007/100880, 2007, A1. Location in patent: Page/Page column 81
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178
[5] Organic Letters, 2013, vol. 15, # 22, p. 5662 - 5665 |
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