4-bromo-1H-pyrrolo[2,3-c]pyridine
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![4-bromo-1H-pyrrolo[2,3-c]pyridine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220811/05d8f562b33f4d76a516c59d3631de78.png "4-bromo-1H-pyrrolo[2,3-c]pyridine")
4-bromo-1H-pyrrolo[2,3-c]pyridine
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CAS No:
69872-17-9
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Formula:
C7H5BrN2
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Chemical Name:
4-bromo-1H-pyrrolo[2,3-c]pyridine
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Synonyms:
4-bromo-1H-pyrrolo[2,3-c]pyridine;4-Bromo-6-azaindole;1H-PYRROLO[2,3-C]-PYRIDINE,4-BROMO-;4-BroM-6-azaindol;4-broMo-1H-pyrrolo[2,3-c]pyridin
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CAS No:
Safety Information
IRRITANT
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
4-bromo-1H-pyrrolo[2,3-c]pyridine Use and Manufacturing
4-bromo-1H-pyrrolo[2, 3-c]pyridine (94c) 4-Bromo-1-tosyl-1H-pyrrolo[2, 3-c]pyridine To a solution of A mixture of 4-bromo-1h-pyrrolo[2, 3-c]pyridine (500 mg, 2.54 mmol), bis(pinacolato)diboron (6.4 g, 25.2 mmol), PdCl2dppf (371 mg, 0.51 mmol), and potassium acetate (746 mg, 7.61 mmol) in 1, 4-dioxane (20 mL) was heated at 120 C. for 16 hours under Ar. The reaction was filtered and concentrated to dryness. The residue was taken up in ethyl acetate (10 mL) and adjusted to pH 7-8 with NaOH. The water layer was adjusted pH to 3-4 with conc. HCl and ethyl acetate (20 mL) added. The water layer were then separated and concentrated to dryness. The residue was taken up in ethyl acetate:ethanol (1:1) and filtered. The resulting liquid was concentrated to dryness. This provided the title compound as a brown solid (350 mg, 85% yield). LCMS (ESI) [M+H]+=163.1.4-Bromo-1H-pyrrolo[2, 3-c]pyridine (5 g, 25.4 mmol, commercially available from, for example, Fluorochem) was dissolved in DMF (50 mL) and cooled in an ice bath under nitrogen, then NaH (a 60% suspension in mineral oil, 1.319 g, 33.0 mmol) was added in small portions and the mixture was stirred for 20 min before addition of tosyl chloride (5.32 g, 27.9 mmol). The mixture was stirred overnight, allowing it to warm to rt, then the mixture was diluted with water (100 mL) and stirred for 30 min, giving a white suspension. This was filtered and the solid washed with water, then dried to give a colourless solid. The crude product was suspended in ether (20 mL) and stirred for 5 min, then diluted with cyclohexane (20 mL) and filtered to give the desired product (7.9 g, 22.49 mmol, 89 % yield) as a colourless solid. (0435) LCMS (2 min High pH): Rt = 1.24 min, [MH]+ = 351/353Step 1 4-Bromo-1-tosyl-1H-pyrrolo[2, 3-c]pyridine To a solution of
Computed Properties
Molecular Weight:197.03
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-bromo-1H-pyrrolo[2,3-c]pyridine
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