Buchwald–Hartwig amination: Iodobenzene → methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate
75% yield, run at 100 °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 | Iodobenzene | C₆H₅I | |
| Reactant | methyl 5-amino-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylate | C₁₀H₁₀FN₃O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Anisole | C₇H₈O | |
| Product | methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate | C₁₆H₁₄FN₃O₂ | 75.07% |
Conditions
- Temperature
- 100 °C
Yield
- 75% of methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate.
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
9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (389 mg, 0.67 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (246 mg, 0.27 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (14.900 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and then heated to 50ºC for 10 minutes. Cesium carbonate (5474 mg, 16.80 mmol), methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate (1500 mg, 6.72 mmol) and Iodobenzene (0.902 ml, 8.06 mmol) were stirred in anisole (29.800 ml), the flask was evacuated and flushed with nitrogen three times and then heated to 50ºC. The catalyst mixture was transferred into the flask with the reactants (by syringe) and the mixture heated to 100 °C for 18 hours. The reaction mixture was
The source
This record comes from experimental reaction archive (ord-a36b48917c9942d1a34637511773ee1f). Open the source and check it against what is on this page.
experimental reaction archive record ord-a36b48917c9942d1a34637511773ee1f 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.
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