HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic Acid → HCID 67521429, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Methoxycarbonyl-5-pyridineboronic acid, pinacol ester | HCID 46738663 | — |
| Reactant | HCID 67389127 | HCID 67389127 | — |
| Reactant | HCID 67520373 | HCID 67520373 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | HCID 67521429 | HCID 67521429 | — |
Reaction Steps
Following the procedures for 3-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester and the benzoic acid, the title compound was prepared from 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (1.1 g, 3.6 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carboxylic acid methyl ester (1.0 g, 3.8 mmol), Pd(PPh3)4 (2 mol %), and Cs2CO3 (2.83 g, 8.7 mmol) in DMF/H2O (24 mL, 5:1). 1H NMR (400 MHz, DMSO-d6): δ=8.90 (s, 1H), 8.61 (d, J=2.0 Hz, 1H), 8.31 (d, J=2.0 Hz, 1H), 8.20-8.07 (m, 5H), 7.96 (brd, J=8.4 Hz, 1H), 7.57 (dt, J=1.0, 8.0 Hz, 1H), 7.49 (dt, J=1.0, 8.0 Hz, 1H); COOH proton not visible. MS(ES+): m/z=349.08 (100) [MH+], 305.09 (8) [MH+—CO2]. HPLC: tR=2.89 min (polar—5 min, ZQ3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178668B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-b757b3f00f24413883242e59ee7b5dff |
| Source note | uspto-grants-2012_05 |