Phenethylamine → benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amine

HRID 55852노트

반응식

HRID 55852 반응식
Cl[C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].C(P[C:27]1[CH:32]=[C:31](PC(C)(C)C)[CH:30]=[CH:29][C:28]=1[C:38]1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C([CH2:60][NH2:61])C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:38]([N:61]([CH3:60])[C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:27]=1

참가 물질

7

반응물 4

HCID 1001PhenethylamineHCID 50915806-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 23676156Sodium t-butoxideHCID 866928022,4Di-tert-butylphosphino-2',4',6'-triisopropyl biphenyl

생성물 1

HCID 53372368benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amine수율 109.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

To a degassed mixture of 6-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2-B) (100 mg, 0.5 mmol), sodium tert-butoxide (576 mg, 6.0 mmol), palladium acetate (22.4 mg, 0.1 mmol) and 2,4 di-tert-butylphosphino-2′,4′,6′-triisopropyl biphenyl (63.0 mg, 0.15 mmol) is added dry toluene (2 mL). After stirring for 5 min, benzylmethylamine (0.09 mL, 0.7 mmol) is added to the reaction mixture, which is stirred at 100° C. for 16 h. The reaction mixture is filtered and the residue washed with EtOAc. The filtrate is concentrated under reduced pressure to afford crude material, which is purified by reverse phase HPLC to yield benzyl-methyl-(2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl)-amine (2-C) (50 mg).

후처리

  1. stirringis stirred at 100° C. for 16 h
  2. filtrationThe reaction mixture is filtered
  3. washthe residue washed with EtOAc
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customto afford crude material, which
  6. customis purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-786dda22219b489b9476bc3888d399d7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433626B2

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