HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Acetamidopyridine-5-boronic acid pinacol ester → N-(5-(6-acetamidopyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Acetamidopyridine-5-boronic acid pinacol ester | HCID 17750202 | — |
| Reactant | N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide | HCID 58015383 | — |
| Product | N-(5-(6-acetamidopyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide | HCID 44548773 | 14% |
Reaction Steps
The titled compound (yield=14%, white solid) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide and 2F (Example 2) were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 2.14 (s, 3H) 3.49 (d, J=5.31 Hz, 2H) 4.78 (t, J=5.31 Hz, 1H) 7.58 (d, J=8.59 Hz, 2H) 8.06-8.18 (m, 3H) 8.18-8.26 (m, 2H) 8.52 (dd, J=8.84, 2.53 Hz, 1H) 9.09 (d, J=1.77 Hz, 1H) 10.73 (s, 1H) 13.00 (s, 1H); ESI-MS: m/z 462.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178555B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-eeb9de39980c42a2b77121a66d03d59e |
| Source note | uspto-grants-2012_05 |