Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Bromophenetole | HCID 68523 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | HCID 67125403 | HCID 67125403 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene tert-butyl alcohol | HCID 22595558 | — |
| Product | HCID 67970318 | HCID 67970318 | — |
Reaction Steps
3.0 mL Toluene/tert-butanol (5:1) are added to a mixture of 130 mg (0.50 mmol) N-[1-methyl-2-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (VIII.1), 100 mg (0.50 mmol) 1-bromo-4-ethoxy-benzene, 80 mg (0.83 mmol) sodium tert-butyrat, 20 mg (0.040 mmol) X-Phos and 10 mg (0.040 mmol) palladium(II) acetate. The mixture is stirred for 10 min at 150° C. under microwave irradiation in a sealed tube. After that time, the mixture is poured into 1 mL 0.1 N HCl. 1 mL conc. ammonia is added and the mixture is extracted with ethyl acetate (3×). The combined organic layers are dried over sodium sulphate and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel; DCM/MeOH 19:1) to yield the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09006450B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-1301d59892a94b949a42a1eb9f74739f |
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| Source note | uspto-grants-2015_04 |
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