Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Amino-5-bromonicotinic acid | HCID 737445 | — |
| Reactant | 1-(Methylsulfonyl)-1H-benzotriazole | HCID 792044 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 62155529 | HCID 62155529 | 64% |
Reaction Steps
A mixture of 2-amino-5-bromo-pyridine-3-carboxylic acid (203 mg, 0.9354 mmol), aniline (87.11 mg, 85.23 μL, 0.9354 mmol), 1-methylsulfonylbenzotriazole (276.7 mg, 1.403 mmol) and DIPEA (241.8 mg, 325.9 μL, 1.871 mmol) in THF (2.0 mL) was heated in the microwave at 160° C. for 10 mins. The reaction mixture was concentrated and the residue partitioned between EtOAc and 2M NaOH. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the product as a yellow solid (174 mg, 64% Yield). 1H NMR (400.0 MHz, DMSO) δ 7.77 (br s, 2H), 8.18 (d, 1H) and 8.32 (d, 1H); ppm; MS (ES+) 293.94.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09096584B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-234e1a0a0f9245a6821d61b0d24857c7 |
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| Source note | uspto-grants-2015_08 |
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