Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1-Methyl-1H-indazole-6-boronic acid | HCID 44118215 | — |
| Reactant | tert-butyl(2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)carbamate | HCID 90433946 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 90463304 | HCID 90463304 | 25% |
Reaction Steps
A mixture of tert-butyl N-[2-([[3-iodo-1-(oxan-2-yl)-1H-pyrazol-4-yl]methyl](methyl)amino)ethyl]carbamate (200 mg, 0.43 mmol, 1.00 equiv), K3PO4 (273 mg, 1.29 mmol, 3.00 equiv), (1-methyl-1H-indazol-6-yl)boronic acid (113 mg, 0.64 mmol, 1.50 equiv) and Pd(dppf)Cl2.CH2Cl2 (70 mg, 0.10 mmol, 0.20 equiv) in ethylene glycol dimethyl ether (20 mL) was stirred under nitrogen at 95° C. overnight. The resulting mixture was cooled to room temperature then concentrated under vacuum. The crude product was purified by Pre-HPLC with the following conditions (1#-Pre-HPLC-005 (Waters)): Column, XBridge Shield RP18 OBD Column, 5 m, 19×150 mm; mobile phase, water with 10 mmol NH4HCO3 and CH3CN (18% CH3CN up to 58% in 10 min, up to 95% in 1 min, down to 18% in 2 min); Detector, UV 254/220 nm to yield 50 mg (25%) of tert-butyl 2-(methyl((3-(1-methyl-1H-indazol-6-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethylcarbamate as a colorless oil. LCMS (method A, ESI): RT=1.16 min, m/z=469.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09133189B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-e1e5ef62261947c89e3143553499024a |
|---|
| Source note | uspto-grants-2015_09 |
|---|
