1,10-Phenanthroline → HCID 59455068, compound

HRID 1401692Notes

Reaction equation

HRID 1401692 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:39]#[C:40][C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=1>C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:39]#[C:40][C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 62657Potassium Phosphate, TribasicHCID 6403901-(Bromoethynyl)-4-chlorobenzene

Product 1

HCID 59455068HCID 59455068, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

8-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (220 mg, 1 mmol) was dissolved in toluene (8-10 mL). Copper sulfate (50 mg, 0.2 mmol), 1,10-phenanthroline (72 mg, 0.4 mmol), potassium phosphate (425 mg, 2 mmol) and 1-(bromoethynyl)-4-chlorobenzene (237 mg, 1.1 mmol) was added and the mixture flushed with nitrogen. The reaction mixture was heated at 80° C. overnight (16 h). Product was detected by LCMS. The reaction mixture was filtered through Celite, washed with DCM. The combined organic layer was concentrated under vacuum to obtain product, which was purified by column chromatography using silica and 60-80% EtOAc in hexane as eluent to obtain product (120 mg) as a brown semi solid. 1H NMR (CDCl3, HCl salt) δ (ppm): 7.52-7.42 (m, 3H), 7.38-7.32 (m, 2H), 7.30 (s, 1H), 7.23-7.20 (d, 1H), 3.62 (s, 2H), 3.02-2.97 (m, 2H), 2.96-2.86 (m 2H), 2.60 (s, 3H).

Workup

  1. customthe mixture flushed with nitrogen
  2. filtrationThe reaction mixture was filtered through Celite
  3. washwashed with DCM
  4. concentrationThe combined organic layer was concentrated under vacuum
  5. customto obtain product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ef4286b5f684408996bb14f2e76f6409
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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