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

HRID 55852ノート

反応式

HRID 55852 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-786dda22219b489b9476bc3888d399d7
出典データセット
uspto-grants-2016_09
特許番号
US09433626B2

反応ノート

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