Lithium Chloride → 5-Bromo-3-furan-3-yl-2-trimethylsilanyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

5-Bromo-3-iodo-pyridin-2-ylamine (12) (390 mg, 1.32 mmol; prepared according to WO0196308), crude acetylene 11 (910 mg), LiCl (56 mg, 1.32 mmol), KOAc (259 mg, 2.64 mmol), Pd(OAc)2 (7.4 mg, 0.03 mmol) in DMF (10 mL) were heated in a sealed tube at 100° C. After 19 h the mixture was partitioned between Et2O and saturated aqueous NH4Cl. The organic layer was separated and the aqueous layer was extracted with Et2O (4×). The combined organic solutions were dried (MgSO4) and concentrated. The residual red oil was purified by PTLC with AcOEt:hexane=1:4 as eluent to yield azaindole 13 (97.9 mg, 22%) as an oil. 1H NMR (400 MHz; CDCl3) δ 0.32 (s, 9H), 6.53 (d, J=0.9 Hz, 1H), 7.51 (s, 1H), 7.55 (t, J=1.6 Hz, 1H), 7.97 (d, J=1.9 Hz, 1H), 8.34 (d, J=2.1 Hz, 1H), 9.09 (brs, NH).

Provenance & Evidence