HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1851759Generated: November 1, 2026
Dimethylformamide → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine
https://huagongshe.com/reaction/1851759
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine | HCID 2756555 | — |
| Reactant | 2-Bromo-6-methoxy-1,3-benzothiazole | HCID 11218765 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine | HCID 24803565 | — |
Reaction Steps
A mixture of 2-bromo-6-methoxy-benzothiazole (1.14 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.23 g, 1.2 eq.), Pd(dppf)Cl2*DCM (170 mg, 0.05 eq.) and 2.0 M aq. K2CO3 (10 ml, 4 eq.) in DMF (20 ml) was heated at 80° C. for 2 h under argon while stirring. Ethyl acetate (200 ml) was subsequently added before concentrating the sol. onto diatomaceous earth in vacuo. Purification by flash chromatography (DCM:methanol, 99:1 to 95:5) provided the title compound (730 mg) as a yellow solid. 1H NMR δ 8.56 (d, 1 H) 7.96 (dd, 1 H) 7.82 (d, 1 H) 7.64 (d, 1 H) 7.07 (dd, 1 H) 6.67 (br. s, 2 H) 6.55 (d, 1 H) 3.83 (s, 3 H); MS m/z (M+H) 258.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08957215B2 |
|---|
| Source dataset | uspto-grants-2015_02 |
|---|
| ORD ID | ord-2c5a9b73acdb47fe8b2b767d01190f93 |
|---|
| Source note | uspto-grants-2015_02 |
|---|
