N-methyl-2-pyrrolidone → 2-Chloro-6-(3-fluorobenzylamino)isonicotinonitrile

HRID 1963882

반응식

HRID 1963882 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[N:9]=1)[C:5]#[N:6].CN1C(=O)CCC1.[F:18][C:19]1[CH:20]=[C:21]([CH2:25][NH2:26])[CH:22]=[CH:23][CH:24]=1>CCOC(C)=O>[Cl:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([NH:26][CH2:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([F:18])[CH:20]=2)[N:9]=1)[C:5]#[N:6]

참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 668533-FluorobenzylamineHCID 7359062,6-Dichloroisonicotinonitrile

생성물 1

HCID 830730972-Chloro-6-(3-fluorobenzylamino)isonicotinonitrile수율 99.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

To a scintillation vial containing 2,6-dichloroisonicotinonitrile (500 mg, 2.89 mmol) was added NMP (6 ml) and (3-fluorophenyl)methanamine (868 mg, 6.94 mmol). The homogenous reaction mixture was capped and heated to 110° C. in a oil bath for 1 hr. The reaction mixture was diluted with EtOAc and washed with sat NaHCO3, H2O and sat NaCl. The organic layer was dried Na2SO4, filtered and concentrated. The crude residue was purified by column chromatography on silica gel (0-20% EtOAc/Hexane) to give 2-chloro-6-(3-fluorobenzylamino)isonicotinonitrile (750 mg, 95%). LCMS (m/z): 262.0 (MH+), retention time=1.03 min.

후처리

  1. customThe homogenous reaction mixture was capped
  2. washwashed
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by column chromatography on silica gel (0-20% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-dd0363d8da1544b588d6c72e1f2f28a4
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415381B2

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