Ammonium Hydroxide → HCID 66673707, compound

Temperature

-10 °C

Triflic anhydride (10 g, 35.4 mmol) was added dropwise to a cold (−40° C.) solution of 5-acetyl-2-hydroxy-benzoic acid methyl ester (6.9 g, 35.4 mmol) and DIPEA (5.3 g, 42.5 mmol) in CH2Cl2 (100 mL). The reaction was warmed to −10° C. and stirred for 16 h. The reaction was warmed to rt, evaporated to dryness in vacuo, and re-dissolved in EtOAc. The organic layer was washed with ½ sat. brine, dried over MgSO4, filtered and evaporated in vacuo. A portion of the crude triflate (5.01 g, 15.3 mmol) was dissolved in DMF (40 mL). Palladium(0)tetrakis(triphenylphosphine) (1.3 g, 1.1 mmol) and zinc cyanide (2.16 g, 18.4 mmol) were added to the flask, and the mixture was heated to 90° C. for 2.5 h. The reaction was cooled to rt and stirred with a 1:1 solution of conc. NH4OH and water (160 mL). The resulting suspension was extracted with ETOAc. The combined organic extracts were washed with ½ sat. brine, dried over MgSO4, filtered and evaporated in vacuo. The title compound was isolated by SiO2 chromatography to yield 439 mg (14%) of a white solid. MS 221.1 (M+NH4)+.

1. temperatureThe reaction was warmed to rt
2. customevaporated to dryness in vacuo
3. dissolutionre-dissolved in EtOAc
4. washThe organic layer was washed with ½ sat. brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated in vacuo
8. temperaturethe mixture was heated to 90° C. for 2.5 h
9. temperatureThe reaction was cooled to rt
10. extractionThe resulting suspension was extracted with ETOAc
11. washThe combined organic extracts were washed with ½ sat. brine
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. customevaporated in vacuo

ORD record

ord-41ed43cc81a942ddb3ecd214dd5810fa

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079860B2