Ethyl bromoacetate → HCID 69755746, compound

Temperature

120 °C

Powdered and flame dried potassium carbonate (1.52 g, 11 mmol, 1.1 eq.) was placed in a round bottom flask together with 60 mL of anhydrous dimethylformamide and kept under inert atmosphere. 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (1.942 g, 10 mmol, 1 eq.) was dissolved in 20 mL of anhydrous DMF and added to the reaction mixture. The reaction was heated to 120° C. under reflux condenser for 1 hour and then solution of ethyl bromoacetate (3.34 g, 2.22 mL, 20 mmol, 2 eq.) in 5 mL of dry DMF was added dropwise to the hot solution. The reaction mixture was then heated to 120° C. for an additional 12 hours. When cooled, the DMF was removed on the rotary evaporator, and diluted with 100 mL of water. The aqueous phase was washed (3×) with 50 mL portions of methylene chloride. The methylene chloride extracts were combined and washed with water and brine and dried over magnesium sulfate. Crude material (3.018 g) was chromatographed on a large Biotage column in 20% ethyl acetate/hexanes. 1.38 g (50% yield) of pure material (bright yellow crystalline powder) was collected. LC MS: AP+281, AP−280.

1. additionadded to the reaction mixture
2. temperatureunder reflux condenser for 1 hour
3. temperatureThe reaction mixture was then heated to 120° C. for an additional 12 hours
4. temperatureWhen cooled
5. customthe DMF was removed on the rotary evaporator
6. additiondiluted with 100 mL of water
7. washThe aqueous phase was washed (3×) with 50 mL portions of methylene chloride
8. washwashed with water and brine
9. dry with materialdried over magnesium sulfate
10. customCrude material (3.018 g) was chromatographed on a large Biotage column in 20% ethyl acetate/hexanes

ORD record

ord-5875fdc206e4445d95a994c428ff6fa8

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06821977B2