Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate → Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate

HRID 717817ノート

反応式

HRID 717817 の反応式
[Cl:1][C:2]1[C:3]([C:19]#[N:20])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>CO.[Pd]>[NH2:20][CH2:19][C:3]1[C:2]([Cl:1])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[N:4]=1

参加物

4

反応物 1

HCID 58515932Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate

生成物 1

HCID 58515976Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate (1.3 g, 4.5 mmol) was stirred in methanol (60 mL), and 5% palladium on carbon (1.0 g) was added. The mixture was degassed three times and placed under a balloon pressure of hydrogen for 4 hours. A solution of 0.5 M sodium methoxide in methanol (45 mL) was added and the mixture was filtered through celite. The filtrates were evaporated and the residue was triturated with dichloromethane. The solids were filtered and washed with dichloromethane to give the desired compound contaminated with 30% dechlorinated byproduct (1.3 g, 100%). LCMS calculated for C14H13ClFN2O2 (M+H)+: m/z=295.1. found: 295.0.

後処理

  1. customThe mixture was degassed three times
  2. additionA solution of 0.5 M sodium methoxide in methanol (45 mL) was added
  3. filtrationthe mixture was filtered through celite
  4. customThe filtrates were evaporated
  5. customthe residue was triturated with dichloromethane
  6. filtrationThe solids were filtered
  7. washwashed with dichloromethane

出典と根拠

ORDレコード
ord-a8aecba26b3d4cb3ae1d26dccdd1052b
出典データセット
uspto-grants-2015_11
特許番号
US09193721B2

反応ノート

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