Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 86669015 | HCID 86669015 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 75409785 | HCID 75409785 | 29% |
Reaction Steps
A stirred mixture of 2-(2-bromo-6-chlorophenyl)-4-chlorothiazolo[5,4-c]pyridine (1.48 g, 4.11 mmol) and copper(I) cyanide (0.45 g, 5.0 mmol) in NMP (20 mL) was heated at 150° C. for 20 minutes. After cooling to room temperature, the mixture was poured into water (250 mL) and the insoluble material was collected by filtration. The solid was then suspended in EtOAc (300 mL) and, after vigorous stirring, was collected by filtration. The filtrate was concentrated under reduced pressure and the resultant residue was purified by column chromatography on silica gel eluting with 25-33% diethyl ether in pentane followed by 0-10% MeOH in DCM to afford the title compound as a pale yellow solid (0.364 g, 29% yield). LCMS (Method E): RT=3.59 min, m/z: 306 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08697708B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-7762ceae2ca84a48bb69454c8172c653 |
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| Source note | uspto-grants-2014_04 |
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