HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate → HCID 90031784, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate | HCID 16217947 | — |
| Reactant | 5-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90031306 | — |
| Catalyst | Sodium Carbonate | HCID 10340 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | HCID 90031784 | HCID 90031784 | 83.2% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Step-i of example-14) (200 mg, 0.361 mmol) was coupled with tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (intermediate 69C) (140 mg, 0.361 mmol) using Pd(dppf)Cl2 (14 mg, 0.018 mmol) and sodium carbonate (114, 0.018 mmol) in DME/water (25/5 ml). This afforded 221 mg (83% yield) of the titled compound. MS: m/z=736.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-da266791f7fa437d8e121b217ff03a9b |
| Source note | uspto-grants-2016_05 |