Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium methanethiolate | HCID 4378561 | — |
| Reactant | 5-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine | HCID 45789788 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57537462 | HCID 57537462 | 100% |
Reaction Steps
5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.16 mmol) was combined with sodium thiomethoxide (151 mg, 2.16 mmol) and dissolved in N,N-dimethylformaldehyde (5 mL). The solution was at 80° C. for 15 hours when additional sodium thiomethoxide (75 mg, 1.08 mmol) was added. The solution was stirred for at 80° C. for 2 hours. Water (50 mL) was added to the reaction mixture, and the precipitate was collected by vacuum filtration to afford 5-Bromo-4-methylsulfanyl-1H-pyrrolo[2,3-b]pyridine (524 mg, 2.16 mmol, >99% yield) as a white solid. 1H-NMR [500 MHz, d6-DMSO] δ: 11.99 (s, 1H), 8.22 (s, 1H), 7.54 (d, 1H), 6.69 (d, 1H), 2.74 (s, 3H); MS [MH+] m/z: 243.0, 244.9
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08158647B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-16b55e095ca24483ba18b19310ac9e3a |
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| Source note | uspto-grants-2012_04 |
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