Buchwald–Hartwig amination: 6-Bromopyridine-2-carboxylic acid → 6-[(4-Methyl-1,3-thiazol-2-yl)amino]pyridine-2-carboxylic acid
0% yield, run at 110 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 6-Bromopyridine-2-carboxylic acid | C₆H₄BrNO₂ | |
| Reactant | 2-Amino-4-methylthiazole | C₄H₆N₂S | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 6-[(4-Methyl-1,3-thiazol-2-yl)amino]pyridine-2-carboxylic acid | C₁₀H₉N₃O₂S | 0% |
Conditions
- Temperature
- 110 °C
Yield
- 0% of 6-[(4-Methyl-1,3-thiazol-2-yl)amino]pyridine-2-carboxylic acid.
Other recorded runs with the same starting material
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.
Procedure
Copied from the source record, unedited
_The aim of this reaction is to synthesize material to check some ideas for route development and see if 'normal' Buchwald conditions is applicable here. IPC.s were taken and the reaction was monitored either by LCMS or HNMR (a crude sample dissolved in DMSO)._ 19/11-2015 14:00 A dried 250 mL rb-flask under nitrogen atmosphere was charged with 4-methylthiazol-2-amine (C0033995, BT250061) (6.61 g, 57.92 mmol), 6-bromopicolinic acid (C0013377, BT249846) (11.7 g, 57.92 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (C0007769, BT234652) (1.326 g, 1.45 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphane (C0018897, BT153355) (2.76 g, 5.79 mmol), SODIUM T-BUTOXIDE (C0006296, BT235115) (16.70 g, 173.76 mmol), Toluene (193 ml) was added and the suspension was heated and sti
The source
This record comes from experimental reaction archive (ord-72695457b0814d8bbec66d3f30d9e87c). Open the source and check it against what is on this page.
experimental reaction archive record ord-72695457b0814d8bbec66d3f30d9e87c from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
More Buchwald–Hartwig amination records
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