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

HRID 55853노트

반응식

HRID 55853 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 (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) was added dry toluene (2 mL). After stirring for 5 min, benzylmethylamine (0.09 mL, 0.7 mmol) was added to the reaction mixture, which was stirred at 100° C. for 16 h. The reaction mixture was filtered and residue washed with EtOAc. The filtrate was concentrated under reduced pressure to afford crude material, which was 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 (50 mg). 1H NMR (Freebase, CDCl3) δ (ppm): 7.80 (bs, 1H), 7.38 (m, 4H), 7.28 (m, 1H), 7.10 (s, 1H), 7.0 (t, 1H), 6.78 (d, 1H), 4.28 (s, 2H), 3.70 (s, 2H), 2.86 (m, 4H), 2.78 (s, 3H), 2.58 (s, 3H).

후처리

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

출처 및 근거

ORD 기록
ord-98776dc874fc4123b5756011dcbf0135
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433626B2

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