3-(Cyanomethyl)pyridine-2-carbonitrile → 6-Amino-8-benzyl-1,7-naphthyridine

HRID 369028

반응식

HRID 369028 반응식
[C:1]([C:3]1[C:8]([CH2:9][C:10]#[N:11])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[CH2:12]([Mg]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.O1CCCC1>[NH2:11][C:10]1[CH:9]=[C:8]2[C:3](=[C:1]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:2]=1)[N:4]=[CH:5][CH:6]=[CH:7]2

참가 물질

5

반응물 2

HCID 46725983-(Cyanomethyl)pyridine-2-carbonitrileHCID 178419663HCID 178419663, 화합물

생성물 1

HCID 232846456-Amino-8-benzyl-1,7-naphthyridine

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-cyano-3-pyridylacetonitrile (2 g, 0.014 mol) in toluene (20 ml) is added benzylmagnesium bromide 8.4 ml, 2N in tetrahydrofuran, 0.17 mol) at ambient temperature. After 1 h the reaction is quenched with a saturated solution of ammonium chloride. The product is extracted with ethyl acetate and the organic layer washed with 2N NaOH and water. The product is purified by flash column chromatography on silica gel (10:3 toluene/acetone) affording the title compound. Mass M+H 236; mp 113-116° C.

후처리

  1. customAfter 1 h the reaction is quenched with a saturated solution of ammonium chloride
  2. extractionThe product is extracted with ethyl acetate
  3. washthe organic layer washed with 2N NaOH and water
  4. customThe product is purified by flash column chromatography on silica gel (10:3 toluene/acetone)

출처 및 근거

ORD 기록
ord-8b5b8840371746999baa1b1e3589ae07
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136821

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