Cesium carbonate → (6-Methyl-pyridin-2-yl)-[1,7]naphthyridin-8-yl-amine

HRID 1787587

반응식

HRID 1787587 반응식
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:19][C:15]1[N:14]=[C:13]([NH:12][C:2]2[N:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 157652-Amino-6-methylpyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 123427128-Chloro-(1,7)naphthyridine

생성물 1

HCID 16118550(6-Methyl-pyridin-2-yl)-[1,7]naphthyridin-8-yl-amine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

8-Chloro-[1,7]naphthyridine (Example A) (0.2 g, 1.2 mmol) and 2-amino-6-methylpyridine (0.13 g, 1.2 mmol) were dissolved in 8 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (145 mg, 0.24 mmol), cesium carbonate (0.63 g, 1.95 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (0.13 g, 0.12 mmol) were added and the reaction mixture was stirred under microwave irradiation for 50 minutes at 150° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 95:5->70:30 gradient). The desired product was obtained as a light yellow solid (98 mg, 34%),

후처리

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 95:5->70:30 gradient)

출처 및 근거

ORD 기록
ord-5937f0fba58341699293691ccde86743
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07511055B2

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