Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | 4-Chloro-1-(toluene-4-sulfonyl)-2-tributylstannanyl-1H-pyrrolo[2,3-b]pyridine | HCID 59432612 | — |
| Reactant | t-Butyl 3-bromo-5,6-dimethoxy-pyrrolo[3,2-b]pyridine-1-carboxylate | HCID 68469784 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68471318 | HCID 68471318 | 68.6% |
Reaction Steps
Bubble a solution of dimethoxyazaindole 11 (0.25 g, 0.70 mmol) and azaindole 26 (0.458 g, 0.77 mmol) in toluene (15 mL) with N2 for 15 min, then add CuI (14 mg, 0.07 mmol) and Pd(PPh3)4 (81 mg, 0.07 mmol) and agitate the mixture with the stream of N2 for 0.5 h, then heat at 120° C. under N2 for 20 h. Purification of the reaction mixture on SiO2 (flash chromatography, 40 g cartridge, elution with EtOAc at 10-30%/heptane) gives bisazaindole 27 (0.28 g, 68%) as a white solid: 1H NMR (CDCl3) δ 8.29 (d, 1H, J=5.4 Hz), 7.86 (s apparent overlapping d, 3H), 7.15 (m, 4H), 6.94 (s, 1H), 3.97 (s, 6H), 2.32 (s, 3H), 1.71 (s, 9H), TLC (EtOAc at 40%/heptane) Rf=0.40.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07786114B2 |
|---|
| Source dataset | uspto-grants-2010_08 |
|---|
| ORD ID | ord-42bc05642b8c4b2fadf73d196dd1e9ef |
|---|
| Source note | uspto-grants-2010_08 |
|---|
