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

HRID 1963882ノート

反応式

HRID 1963882 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 830730972-Chloro-6-(3-fluorobenzylamino)isonicotinonitrile収率 99.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dd0363d8da1544b588d6c72e1f2f28a4
出典データセット
uspto-grants-2013_04
特許番号
US08415381B2

反応ノート

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