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

HRID 495267

반응식

HRID 495267 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[CH3:8][C:4]1[N:3]=[C:2]([NH:1][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 7961BromobenzeneHCID 157652-Amino-6-methylpyridineHCID 23676156Sodium t-butoxide

생성물 1

HCID 219935396-methyl-N-phenylpyridin-2-amine수율 35.7%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
10 °C

실험 절차

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 10° 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.

후처리

  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. temperaturecooled to 22 C
  4. customAfter quenching with 50 ml water
  5. extractionthe product was extracted with 20 ml ethyl acetate
  6. washwashed with 15 ml water
  7. extractionThe product was extracted with 50 ml of 1M hydrochloric acid
  8. extractionextraction with 20 ml ethyl acetate
  9. customthe product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-6bddddf6475e4d0d9015f38bdd96fc70
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538931B2

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