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

HRID 717817노트

반응식

HRID 717817 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a8aecba26b3d4cb3ae1d26dccdd1052b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193721B2

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