1,10-Phenanthroline → HCID 57930454, compound

HRID 2198359Notes

Reaction equation

HRID 2198359 reaction equation
[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

Participants

6

Reactant 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, compound

Product 1

HCID 57930454HCID 57930454, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bdce72d314ca466881fa94ff64693fa8
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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