Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Chlorophenylboronic acid | HCID 74299 | — |
| Reactant | HCID 21109713 | HCID 21109713 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 21109712 | HCID 21109712 | 38.3% |
Reaction Steps
A mixture of 77 mg (0.25 mmol) 6-benzylamino-5-bromo-nicotinic acid, 58 mg (0.375 mmol) 4-chlorophenyl boronic acid, 9.1 mg 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium (II) dichloromethane complex 1:1 and 0.38 mL 2N Na2CO3 aq. in 0.5 mL water and 2 mL dioxane was heated to 85° C. for 20 h. Formic acid was added, filtered and the mixture was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/HCOOH. The combined product fractions were evaporated to yield 32.4 mg (38%) of the title compound. MS (m/e): 337.3 (M−H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07229999B2 |
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| Source dataset | uspto-grants-2007_06 |
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| ORD ID | ord-d4642aafde3a4cf5b39c771d78a1f18c |
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| Source note | uspto-grants-2007_06 |
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