1,10-Phenanthroline → HCID 57930454, 화합물

HRID 1775973노트

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HRID 1775973 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:5]2=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:39]#[C:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([F:49])[CH:42]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:39]#[C:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[C:43]([F:49])[CH:42]=1)[C:6]1[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][C:5]2=1

참가 물질

6

반응물 4

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 155083736-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleHCID 59455074HCID 59455074, 화합물

생성물 1

HCID 57930454HCID 57930454, 화합물수율 18.1%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

6-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (100 mg, 0.45 mmol) was mixed with CuSO4.5H2O (23 mg, 0.090 mmol), 1,10-phenanthroline (33 mg, 0.18 mmol), K3PO4 (192 mg, 0.90 mmol) and 4-(bromoethynyl)-2-fluoro-1-methoxybenzene (113 mg, 0.49 mmol) in toluene (5 ml). The reaction mixture was purged with nitrogen and heated at 80° C. for 16 h. Product was detected by LCMS. The reaction mixture was filtered through Celite and Celite bed was rinsed with dichloromethane. Combined organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (100-200 mesh) eluting with 60-80% ethyl acetate in hexane to obtain 6-chloro-9-((3-fluoro-4-methoxyphenyl)ethynyl)-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (30 mg). 1H NMR (CDCl3) FREE BASE 7.42 (d, 2H), 7.25 (m, 3H), 6.95 (t, 1H), 3.90 (s, 3H), 3.70 (s, 2H), 2.80 (m, 4H), 2.56 (s, 3H).

후처리

  1. customThe reaction mixture was purged with nitrogen
  2. filtrationThe reaction mixture was filtered through Celite and Celite bed
  3. washwas rinsed with dichloromethane
  4. concentrationCombined organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (100-200 mesh)
  6. washeluting with 60-80% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-c5f13db71d8c4465ab37de840a5466a8
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260429B2

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