Hydrochloric Acid → HCID 59553595, compound

Temperature

100 °C

To a mixture of 4-bromoanisole (1.00 mL, 8.0 mmol), N-(diphenylmethylene)glycine ethyl ester (2.14 g, 8.0 mmol) and potassium phosphate tribasic (5.11 g, 24.1 mmol) in toluene (15 mL) under an argon atmosphere were added tri-tert-butylphosphine (79 μl, 0.32 mmol) and tris(dibenzylideneacetone)palladium(0) (147 mg, 0.16 mmol). The reaction mixture was stirred for 24 h at 100° C. It was filtered over Hyflo® and washed with toluene. The filtrate was concentrated and diluted with methanol (5 mL). At 5° C. aqueous methylamine (41% in water, 4.74 mL, 56.1 mmol) was added dropwise and stirring was continues for 22 h at ambient temperature. The resulting suspension was concentrated and the residue was taken in THF (5 mL), before aqueous HCl (1M, 40 mL, 40 mmol) was added. After stirring for 4 h at ambient temperature it was extracted with tert-butylmethylether, the organic layers were washed with aqueous HCl (1M). The aqueous. layers were washed with ethyl acetate and concentrated in vacuo. The residue was separated between THF and aqueous NaOH (1M). The organic layer was dried over sodium sulfate and concentrated affording the title compound (943 mg, 61%) as a light brown oil. MS m/e: 150.2 [M-Me-NHMe+H]+).

1. filtrationIt was filtered over Hyflo®
2. washwashed with toluene
3. concentrationThe filtrate was concentrated
4. additiondiluted with methanol (5 mL)
5. stirringstirring
6. waitwas continues for 22 h at ambient temperature
7. concentrationThe resulting suspension was concentrated
8. additionwas added
9. stirringAfter stirring for 4 h at ambient temperature it
10. extractionwas extracted with tert-butylmethylether
11. washthe organic layers were washed with aqueous HCl (1M)
12. washlayers were washed with ethyl acetate
13. concentrationconcentrated in vacuo
14. customThe residue was separated between THF and aqueous NaOH (1M)
15. dry with materialThe organic layer was dried over sodium sulfate
16. concentrationconcentrated

ORD record

ord-42818330db3a49d5ab77b613e50f3de5

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829563B2