HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate → 5-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate | HCID 136960277 | — |
| Solvent | Toluene trifluoroacetic acid | HCID 69846924 | — |
| Product | 5-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine | HCID 136492681 | 42.6% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (66 mg, 0.116 mmol) was deprotected in TFA/toluene (5/5 mL) to afford 23 mg (34% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.82-8.81 (d, 1H), 8.58 (s, 1H), 7.87 (s, 1H), 7.58-7.45 (m, 4H), 7.23-7.11 (m, 5H), 6.577-6.570 (d, 1H), 4.48-4.44 (t, 2H), 3.56-3.52 (d, 2H), 3.24-3.15 (m, 5H), 2.15-2.03 (m, 4H). MS: m/z=466.5 (M+1), HPLC: 96.98% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-46415daed35942f4b8a26be31a03ad82 |
| Source note | uspto-grants-2016_05 |