Buchwald–Hartwig amination: 6-Chloronicotinamide → 6-[[4-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

100 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.

• 6-[[2-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide1%
• 6-[[3-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide0%

Copied from the source record, unedited

To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.021 g, 0.03 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (4-(trifluoromethyl)phenyl)methanamine (0.097 mL, 0.68 mmol). The reaction was run in microwave at 100 °C for 4h. The compound was purified by preparative HPLC on a Kromasil C8 column (10 µm 250x20 ID mm) using a gradient of 51-55% acetonitrile in H2O/ACN/FA 95/5/0.2 buffer, over 25 minutes with a flow of 19 mL/min. The compounds were detected by UV at 270nm. 6-(4-(trifluoromethyl)benzylamino)nicotinamide (7.40 mg, 7.40 %) was obtained.

This record comes from experimental reaction archive (ord-92bacb0740454b4398d7f3969518ce26). Open the source and check it against what is on this page.

• experimental reaction archive record ord-92bacb0740454b4398d7f3969518ce26 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

  experimental record · quality medium · source

experimental reaction record.