HCID 59375369, 화합물 → HCID 59375367, 화합물

HRID 2193012노트

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HRID 2193012 반응식
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[N:15][CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.[CH:17]([Mg]Br)([CH3:19])[CH3:18]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ni+2]>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[N:15][CH:14]=[CH:13][C:5]=1[C:6]([CH:17]([CH3:19])[CH3:18])=[N:7]2

참가 물질

5

반응물 2

HCID 59375369HCID 59375369, 화합물HCID 178418365HCID 178418365, 화합물

생성물 1

HCID 59375367HCID 59375367, 화합물

시약·촉매·용매 2

HCID 98715851,2-Bis(diphenylphosphino)ethane nickel(II) chloride촉매HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

To a solution of 1,6-dichloropyrido[4,3-c]-1,6-naphthyridine (50 mg, 0.200 mmol) and 1,2-bis(diphenylphosphino)ethanenickel(II) chloride (1.056 mg, 1.999 μmol) in THF (0.4 mL). The mixture was cooled to −10° C. in a methanol-ice bath, and isopropylmagnesium bromide (220 μl 0.220 mmol, 1 M in THF) was added dropwise. The reaction mixture was stirred at −10° C. for 30 min. The mixture was then allowed to warm to room temperature and then stirred for 30 min. The reaction mixture was quenched with aqueous ammonium chloride (saturated), and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford 1-chloro-6-isopropylpyrido[4,3-c]-1,6-naphthyridine as a red solid. LRMS (APCI) calc'd for (C14H13ClN3) [M+H]+, 258.1; found 258.0.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 30 min
  3. customThe reaction mixture was quenched with aqueous ammonium chloride (saturated)
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3e0d4e46cef9472f943db13e06e4b100
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329722B2

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