HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 6-Amino-5-benzothiazol-2-yl-[3,4']bipyridinyl-2'-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 4-iodopicolinate | HCID 22742038 | — |
| Reactant | 3-(1,3-Benzothiazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine | HCID 57416513 | — |
| Reactant | 4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester | HCID 67520536 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 6-Amino-5-benzothiazol-2-yl-[3,4']bipyridinyl-2'-carboxylic acid methyl ester | HCID 67520834 | — |
Reaction Steps
Following the procedure for 4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester, the title compound was prepared from 3-benzothiazol-2-yl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine (BB8) (1.41 g, 4.0 mmol), 4-iodopyridine-2-carboxylic acid methyl ester (0.85 g, 3.2 mmol), Pd(PPh3)4 (2 mol %) and Cs2CO3 (2.5 g, 7.7 mmol) in dioxane/water (5:1; 18 mL). 1H NMR (CD3OD, 300 MHz): δ=4.01 (s, 3H), 7.38-7.45 (m, 2H), 7.70 (dd, J=7.2, 2.4 Hz, 1H), 7.85 (d, J=6.8 Hz, 1H), 7.95 (d, J=6.8 Hz, 1H), 8.21 (d, J=2.4 Hz, 1H), 8.31 (d, J=2.4 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 8.70 (d, J=7.2 Hz, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178668B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-49e39a8154a94179b139f7601454b6bf |
| Source note | uspto-grants-2012_05 |