Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 67323489 | HCID 67323489 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 67324111 | HCID 67324111 | 10% |
Reaction Steps
(4-(4-(4-Bromophenyl)thiazol-2-yl)tetrahydro-2H-pyran-4-yl)methanamine (200 mg, 0.56 mmol), zinc cyanide (53 mg, 0.45 mmol), and DMF (2 mL) were placed in microwave tube and degassed. 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride (41 mg, 0.05 mmol) was added. Reaction was microwaved at 200° C. for 10 min intervals until complete. The reaction was quenched with ammonium hydroxide/water (1:4) and washed with ethyl acetate. Organic layer was dried over sodium sulfate. Crude was purified using silica chromatography with an ethyl acetate wash followed by 10% Methanol in dichloromethane with 1% triethylamine to yield 4-(2-(4-(aminomethyl)tetrahydro-2H-pyran-4-yl)thiazol-4-yl)benzonitrile (20 mg, 10% yield). MS (ESI) m/z: Calculated for C16H17N3OS: 299.11. found: 300.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08901156B2 |
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| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-cb34ccb0818142ba9b4c2f81a717e00b |
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| Source note | uspto-grants-2014_12 |
|---|
