Triethylamine → HCID 69960826, compound

Temperature

90 °C

A mixture of tert-butyl acrylate (98%; 137 mL; 916 mmol), triethylamine (100 mL; 720 mmol), tri-O-tolylphosphine (97%; 6.30 g; 20 mmol), Pd(OAc)2 (1.80 g; 8 mmol), and NMP (90 mL) was degassed three times. The mixture was heated to 90° C., and a solution of 2-methoxy-5-bromopyridine 1-2(50.0 g; 266 mmol) and NMP (10 mL) was added via addition funnel over 1 hour, maintaining the reaction temperature at 90° C. The reaction was heated for 12 hours after complete addition. The reaction mixture was cooled down to room temperature after completion of the reaction. To the reaction mixture was added toluene (400 mL), and the resulting solution was then passed through a pad of Solka Flok. The filter cake was washed with toluene (270 mL). The toluene solution was washed with water (3×540 mL). An aqueous solution of sodium hypochlorite (NaClO) (2.5%; 200 mL) was slowly added to the toluene solution keeping the temperature about 30° C. The reaction was aged 50 min with a vigorous stirring. The organic layer was separated, washed with water (540 mL) three times, and followed by saturated aqueous NaCl (270 mL). The organic layer was concentrated to oil. The oil was dissolved in 270 mL hexanes and loaded onto to a silica gel (90 g) pad. The silica gel pad was washed with hexanes (73 mL). The product 1-3was eluted with EtOAc:hexane (1:8; v/v) in about 730 mL. The yellow solution was concentrated to oil (126 g; 49.2 wt %; 98.4% yield). The crude oil was used for the next reaction without further purification. Authentic sample was obtained by further concentration of the oil.

1. customwas degassed three times
2. temperaturemaintaining the reaction temperature at 90° C
3. temperatureThe reaction was heated for 12 hours
4. additionafter complete addition
5. temperatureThe reaction mixture was cooled down to room temperature
6. customafter completion of the reaction
7. washThe filter cake was washed with toluene (270 mL)
8. washThe toluene solution was washed with water (3×540 mL)
9. additionAn aqueous solution of sodium hypochlorite (NaClO) (2.5%; 200 mL) was slowly added to the toluene solution
10. customthe temperature about 30° C
11. customThe organic layer was separated
12. washwashed with water (540 mL) three times
13. concentrationThe organic layer was concentrated to oil
14. dissolutionThe oil was dissolved in 270 mL hexanes
15. washThe silica gel pad was washed with hexanes (73 mL)
16. washThe product 1-3was eluted with EtOAc:hexane (1:8; v/v) in about 730 mL
17. concentrationThe yellow solution was concentrated to oil (126 g; 49.2 wt %; 98.4% yield)
18. customThe crude oil was used for the next reaction without further purification
19. customAuthentic sample was obtained by further concentration of the oil

ORD record

ord-5b7bb38fda07440d868eb917716a57c8

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06472403B2