HCID 59375369、化合物 → HCID 59375367、化合物

HRID 2193012ノート

反応式

HRID 2193012 の反応式
[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

参加物

5

反応物 2

HCID 59375369HCID 59375369、化合物HCID 178418365HCID 178418365、化合物

生成物 1

HCID 59375367HCID 59375367、化合物

試薬・触媒・溶媒 2

HCID 98715851,2-Bis(diphenylphosphino)ethane nickel(II) chloride触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e0d4e46cef9472f943db13e06e4b100
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

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