Ammonium Chloride → 2-Amino-6-(2-furyl)-5-(4-methoxy-3-pyridyl)-3-pyridinecarbonitrile

HRID 353224노트

반응식

HRID 353224 반응식
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].[Cl-].[NH4+:17]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:4]#[N:5])=[CH:6][C:7]([C:8]2[CH:7]=[N:17][CH:13]=[CH:14][C:10]=2[O:11][CH3:12])=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 129921342-Amino-5-bromo-6-(2-furyl)nicotinonitrile

생성물 1

HCID 227079912-Amino-6-(2-furyl)-5-(4-methoxy-3-pyridyl)-3-pyridinecarbonitrile수율 56%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-amino-5-bromo-6-(2-furyl)nicotinonitrile (1.80 g, 6.82 mmol), 2-methoxy-5-(1,1,1-tributylstannyl)pyridine (5.20 g, 13.1 mmol) and dichlorobis(triphenylphosphine) palladium (II) (480 mg, 0.634 mmol) in N,N-dimethylformamide (18 ml) was stirred at 80° C. for 2 hours in a nitrogen atmosphere. After cooling as it was, the reaction solution was diluted with ethyl acetate and an aqueous saturated solution of ammonium chloride. The organic layer was washed with an aqueous saturated solution of ammonium chloride (×2), then dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=8:1, 4:1), and then suspended in diethyl ether. The resulting solid was collected by filtration and washed with diethyl ether, to give the title compound (1.12 g, 56%) as a yellow solid.

후처리

  1. temperatureAfter cooling as it
  2. washThe organic layer was washed with an aqueous saturated solution of ammonium chloride (×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=8:1, 4:1)
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-4562e47e2bd243ea824616e00c0b0e90
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750232B2

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