Réaction #1884949

Équation de réaction

4,7-dibromo-pyridal[2,1,3]thiadiazole

2-(tributylstannyl)thiophene

→

crude product

4,7-dithienyl[1,2,5]thiadiazolo[3,4-c]pyridine

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Autrecap
2. 2
   TempératureUpon cooling
3. 3
   Lavageeluting with methylene chloride (200 mL)
4. 4
   AutreAll volatiles were removed in vacuo

Mode opératoire

A 5 mL microwave tube was charged with 4,7-dibromo-pyridal[2,1,3]thiadiazole (PTBr2, 0.556 g, 1.885 mmol), 2-(tributylstannyl)thiophene (Bu3Sn—Th, 1.477 g, 3.957 mmol), Pd(PPh3)4 (0.020 g, 0.018 mmol), toluene (3 mL), and sealed with a teflon cap. The reaction mixture was heated to 120° C. for 3 minutes, 140° C. for 3 minutes, and 170° C. for 36 minutes, using a Biotage microwave reactor. Upon cooling, the residue was passed through a short silica plug eluting with methylene chloride (200 mL). All volatiles were removed in vacuo to give the crude product as a red solid. The solid was slurried in MeOH (100 mL), sonicated for 10 minutes, and filtered. The solid was washed with copious amounts of MeOH and then dried under vacuum for 24 hours. The product was collected as a bright red solid. Recovered yield: 535 mg (94%). 1H NMR (CD2Cl2): δ 8.81 (s, 1H, PT-CH), 8.68 (d, 3JH-H=4 Hz, 1H, Th′—CH), 8.11 (d, 3JH-H=4 Hz, 1H, Th—CH), 7.61 (d, 3JH-H=5 Hz, 1H, Th′—CH), 7.51 (d, 3JH-H=5 Hz, 1H, Th—CH), 7.27 (dd, 3JH-H=4 Hz, 3JH-H=4 Hz 1H, Th′—CH), 7.23 (dd, 3JH-H=4 Hz, 3HH-H=4 Hz 1H, Th—CH), 13C{1H} NMR (CD2Cl2): 155.50, 148.62, 146.91, 142.53 (s, quaternary), 141.28 (s, PT-CH), 137.18 (s, quaternary), 131.97 (s, Th′—CH), 131.00 (s, Th′—CH), 129.40 (s, Th—CH), 128.61 (s, Th—CH), 128.38 (s, Th′—CH), 127.88 (s, Th—CH), 121.00 (s, quaternary). Anal. Calcd. for C13H7N3S3: C, 51.80; H, 2.34; N, 13.94. Found: C, 51.8; H, 2.40; N, 13.7%. UV-vis: (o-DCB) λmax=302, 470 nm, λonset=550 nm, ε=22150 cm−1M−1. PL: (o-DCB) λmax=607 nm. HRMS (EI) m/z, calcd for C13H7N3S3 (M+): 300.98; found: 301.

Source