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1,10-Phenanthroline → 8-chloro-2-methyl-5-((6-methylpyridin-3-yl)ethynyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401696
Notes
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Reaction equation

HRID 1401696 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.C(=O)([O-])[O-].[K+].[K+].Br[C:37]#[C:38][C:39]1[CH:40]=[CH:41][C:42]([CH3:45])=[N:43][CH:44]=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:37]#[C:38][C:39]3[CH:44]=[N:43][C:42]([CH3:45])=[CH:41][CH:40]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 120404695-(2-Bromoethynyl)-2-methylpyridine

Product 1

HCID 594549138-chloro-2-methyl-5-((6-methylpyridin-3-yl)ethynyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalyst
HCID 1140TolueneSolvent2×

Conditions

Temperature
85 °C

Procedure

8-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (56 mg, 0.255 mmol) was dissolved in toluene and copper sulfate (6.3 mg. 0.0255 mmol) was added, followed by 1,10-phenanthroline (9.18 mg, 0.051 mmol) and potassium carbonate (70.38 mg, 0.51 mmol). 5-(Bromoethynyl)-2-methylpyridine (50 mg, 0.255 mmol) dissolved in toluene was added and the mixture purged with nitrogen in it. The reaction mixture was heated at 85° C. overnight. The reaction was monitored by TLC and LCMS. Toluene was concentrated under vacuum and the residue washed with water. The crude product was purified by column chromatography using 0-3% MeOH:DCM as eluent, to give the product as a yellow solid. 1H NMR (CDCl3, freebase) δ (ppm): 8.65 (s, 1H), 7.70 (d, 1H), 7.48 (d, 1H), 7.38 (s, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 3.60 (s, 2H), 2.96 (m, 2H), 2.80 (m, 2H), 2.60 (s, 3H), 2.56 (s, 3H).

Workup

  1. additionwas added
  2. customthe mixture purged with nitrogen in it
  3. concentrationToluene was concentrated under vacuum
  4. washthe residue washed with water
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-1f6a2f70fc484b7c9a8fdd8481f0bcbb
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08907097B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes