| Identification | Back Directory | [Name]
1-Methyl-1H-pyrrolo[2,3-b]pyridine | [CAS]
27257-15-4 | [Synonyms]
1-Methyl-7-azaindole
1-Methylpyrrolo[2,3-b]pyridine
1-Methyl-1H-pyrrolo[2,3-b]pyridine
1H-Pyrrolo[2,3-b]pyridine, 1-Methyl- | [Molecular Formula]
C8H8N2 | [MDL Number]
MFCD09743451 | [MOL File]
27257-15-4.mol | [Molecular Weight]
132.16 |
| Chemical Properties | Back Directory | [Boiling point ]
112-116 °C(Press: 21 Torr) | [density ]
1.107 g/cm3(Temp: 22 °C) | [storage temp. ]
2-8°C | [pka]
5.35±0.30(Predicted) | [Appearance]
Light yellow to green yellow Liquid |
| Hazard Information | Back Directory | [Uses]
N-Methyl-d3-7-azaindole is a labeled reactant used in the preparation of blue fluorescent amino acids as in vivo building blocks for protein engineering. | [Synthesis]
GENERAL METHODS: Preparation of known compound 1a: 7-azaindole (2 g, 16.95 mmol) and anhydrous DMF (10 mL) were added to a dry round-bottomed flask equipped with a magnetic stirring bar under nitrogen atmosphere. The reaction mixture was cooled to 0 °C, 60% sodium hydride (1.2 eq.) was added in batches and stirring was continued for 1 h at this temperature. Subsequently, iodomethane (1.1 eq.) was added slowly and dropwise, keeping the reaction temperature at 0 °C and continuing to stir for 1 hour. Upon completion of the reaction, the reaction was quenched with ice-cold water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1-methyl-7-azaindole in quantitative yield. | [References]
[1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 309 - 313
[2] Green Chemistry, 2017, vol. 19, # 23, p. 5559 - 5563
[3] Organic Letters, 2013, vol. 15, # 22, p. 5718 - 5721
[4] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 2, p. 255 - 267
[5] Journal of Natural Products, 2009, vol. 72, # 12, p. 2199 - 2202 |
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