ChemicalBook CAS DataBase List 3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE

3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE synthesis

5synthesis methods

Product Name:3-BROMO-5-(2-PYRROLIDINYL)PYRIDINE
CAS Number:71719-06-7
Molecular formula:C9H11BrN2
Molecular Weight:227.1

64319-85-3 Synthesis

3-broMo-5-(3,4-dihydro-2H-pyrrol-5-yl)pyridine

64319-85-3
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71719-06-7
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Yield:71719-06-7 90%

Reaction Conditions:

with sodium tetrahydroborate;acetic acid in methanol;acetonitrile at -40 - 20; for 0.166667 h;

Steps:

3-l3romo-5-(2-pyrrolidinyl)-pyridine (3):

A solution of compound 2 (2.0 g, 8.8 mmol) in 80 mE of 80:20 methanol/acetic acid was cooled at -40° C. with dry iceacetonitrile bath. To this reaction mixture sodium borohydride (747 mg, 19.75 mmol) was added portion wise over 10 mm with vigorous stirring. During the course of the addition, the temperature rose to -20° C. After warming to room temperature, most of the solvent was removed with a rotary evaporatot Water (200 mE) was added and the solution was made basic with NaOH and extracted with DCM (2x90 mE). The combined extracts were washed with brine, dried over K2C03, and evaporated. The residue was purified by flash chromatography on a silica gel column (10x4 cm) eluting with 1: 1 ethyl acetate-methanol afforded racemic 3 as a yellow oil: yield 1.8 g (90%); ‘H NMR (400 MHz, CDC13) ? 1.56-1.66 (m, 1H), 1.81-1.95 (m, 3H), 2.16-2.25 (m, 1H), 3.00-3.06 (m, 1H), 3.11-3.17 (m, 1H), 4.15 (t, 1H, J=7.6 Hz),7.88 (t, 1H, J=1.6 Hz), 8.46 (d, 1H, J=2.0 Hz) and 8.50 (d,1H, J=2.4 Hz); ‘3C NMR (100 MHz, CDC13) ? 25.6, 34.7,47.1, 59.3, 120.9, 136.8, 142.9, 146.8 and 149.2.

References:

US2016/375131,2016,A1 Location in patent:Paragraph 0082