Bromobenzene → 6-methyl-N-phenylpyridin-2-amine

To a flask were added 2.2 g of 2-amino-6-methylpyridine, 3.1 g of bromobenzene, 2.7 g of sodium tert-butoxide, and 50 ml toluene. The mixture was purged thoroughly with nitrogen and 62 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthalenehthalene and 22 mg of palladium acetate were added. The reaction mixture was heated to 100 C for 16 hours, and then cooled to 22 C. After quenching with 50 ml water, the product was extracted with 20 ml ethyl acetate, and washed with 15 ml water. The product was extracted with 50 ml of 1M hydrochloric acid, and then basified with aqueous ammonium hydroxide. Following extraction with 20 ml ethyl acetate, the product was purified by silica gel chromatography using a gradient from 10% ethyl acetate in hexane to 15% ethyl acetate in hexane, resulting in 1.3 g of a yellow-orange oil.

1. customThe mixture was purged thoroughly with nitrogen and 62 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthalenehthalene and 22 mg of palladium acetate
2. additionwere added
3. temperatureThe reaction mixture was heated to 100 C for 16 hours
4. temperaturecooled to 22 C
5. customAfter quenching with 50 ml water
6. extractionthe product was extracted with 20 ml ethyl acetate
7. washwashed with 15 ml water
8. extractionThe product was extracted with 50 ml of 1M hydrochloric acid
9. extractionextraction with 20 ml ethyl acetate
10. customthe product was purified by silica gel chromatography

ORD-Eintrag

ord-55603c15e176472c955c87535a0f5789

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09011734B2