1,10-Phenanthroline → (E)-2,8-dimethyl-5-(2-(pyridin-4-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401503Notes

Reaction equation

HRID 1401503 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH:39]=[C:40]([C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1)[CH3:41]>CN(C=O)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6](/[CH:39]=[C:40](/[C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)\[CH3:41])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 59454985(E)-2,8-dimethyl-5-(2-(pyridin-4-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleYield 52.6%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (200 mg, 1 mmol), copper sulfate (50 mg, 0.2 mmol), 1,10-phenanthroline (72 mg, 0.4 mmol), potassium phosphate (425 mg, 2 mmol) and 4-(1-bromoprop-1-en-2-yl)pyridine (237 mg, 1.2 mmol) were mixed in DMF (10 mL) and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 80° C. The reaction mixture was diluted with EtOAc and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% MeOH in DCM) to obtain (E)-2,8-dimethyl-5-(2-(pyridin-4-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (167 mg) as a brown semi solid that was further purified by HPLC to obtain the product as the TFA salt. 1HNMR (DMSO, TFA salt) δ (ppm): 8.40 (m, 2H), 7.20 (s, 1H), 7.10 (m, 3H), 6.95 (d, 1H), 6.86 (d, 1H), 4.40 (m, 2H), 4.22 (m, 2H), 2.90 (s, 3H), 2.80 (m, 2H), 2.38 (s, 3H), 2.30 (s, 3H).

Workup

  1. customthe reaction mixture was purged with nitrogen
  2. additionThe reaction mixture was diluted with EtOAc
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (10% MeOH in DCM)

Sources & evidence

ORD record
ord-74e5bb29b08f480e90d4810aad16a301
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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