ChemicalBook CAS DataBase List IN1306, 3,6-Bis(5-bromopyridin-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

IN1306, 3,6-Bis(5-bromopyridin-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione synthesis

4synthesis methods

Product Name:IN1306, 3,6-Bis(5-bromopyridin-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
CAS Number:777079-50-2
Molecular formula:C16H8Br2N4O2
Molecular Weight:448.07

141-03-7
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97483-77-7 Synthesis

97483-77-7
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$10.00/5g

IN1306, 3,6-Bis(5-bromopyridin-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

777079-50-2
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Yield:777079-50-2 18%

Reaction Conditions:

with iron(III) chloride;tert-Amyl alcohol;sodium at 90; for 25 h;Inert atmosphere;

Steps:

4.6.4 Br-DPP

Under nitrogen atmosphere, sodium (385mg, 17mmol), FeCl₃ (17.3mg, 0.11mmol), and dry tert-amyl alcohol (8.4mL) were heated to 90°C until the sodium was dissolved. 5-bromo-2-cyanopyridine (1.53g, 8.4mmol) was added and then the mixture was heated to 90°C. A solution of di-n-buthylsuccinate (769mg, 3.3mmol) in dry tert-amyl alcohol (3.3mL) was added dropwise for 1h. After stirring for 24h, acetic acid (3.3mL) was added. The mixture was then heated to 120°C. After stirring for 1h, the precipitate was filtered and washed with water, methanol, hexane, and CH₂Cl₂, and dried under vacuum to obtain a dark red solid. Yield: 264mg, 18%. ¹H NMR (400MHz, DMSO-d₆) δ=8.40 (d, 2H, J=8.4Hz), 8.88 (s, 2H), 8.92 (d, 2H, J=8.8Hz), 11.38 (s, 2H); IR (KBr, cm^-1) ν_max 3166 (NH), 1645 (amide C=O stretch), 1613, 1458, 1413; MALDI-MS calcd for C₁₆H₉Br₂N₄O₂ [M+H]⁺ 448.9; Found 448.9. Anal. Calcd for C₁₆H₈Br₂N₄O₂: C 42.89, H 1.80, N 12.50; Found: C 42.51, H 1.41, N 12.31.