HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 6-bromo-5-fluoropyridine-2-carboxylate → Methyl 6-(2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl)-5-fluoropicolinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 6-bromo-5-fluoropyridine-2-carboxylate | HCID 46311204 | — |
| Reactant | (2-(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-yloxy)triisopropylsilane | HCID 66652369 | — |
| Product | Methyl 6-(2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl)-5-fluoropicolinate | HCID 66655918 | 90% |
Reaction Steps
Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.0 equiv.) and (2-(3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-yloxy)triisopropylsilane (1.6 equiv.) at 100° C. for 30 min in the microwave to give methyl 6-(2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl)-5-fluoropicolinate in 90% yield. LC/MS=325.9 (MH+), Rt=0.81 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 1.59 (s, 6 H), 4.00 (s, 3 H), 7.15 (d, J=9.00 Hz, 2 H), 7.62-7.68 (m, 1 H), 8.23-8.29 (m, 1 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09173883B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-b204ea8533154ff58138a463866adc36 |
| Source note | uspto-grants-2015_11 |