Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-Methylpyridine-3-boronic acid | HCID 2762708 | — |
| Reactant | HCID 86663061 | HCID 86663061 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 66605878 | HCID 66605878 | — |
Reaction Steps
2-Bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide 325D (100 mg, 0.267 mmol), 5-methylpyridin-3-ylboronic acid (51.1 mg, 0.373 mmol), PdCl2(dppf)-CH2Cl2 adduct (10.88 mg, 0.013 mmol), and Na2CO3 (2M) (0.666 mL, 1.333 mmol) were mixed with DME (4 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 110° C. in microwave for 1 hr. The mixture was filtered and then purified using preparative HPLC to give titled product. MS (ESI) m/z 387.97 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.33 (s, 1H), 9.25 (s, 1H), 8.52 (s, 1H), 8.44 (s, 1H), 8.43 (s, 1H), 8.36 (s, 1H), 8.09 (d, 1H, J=8.6), 7.87 (s, 1H), 7.23 (s, 1H), 7.03 (dd, 1H, J=8.9, 2.1), 3.81 (m, 4H), 3.25 (m, 4H), 2.44(s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815840B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-f55fc5b34b634c44805114a0011caf03 |
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| Source note | uspto-grants-2014_08 |
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