2-Bromo-5-methylpyridine → HCID 68284376, compound

HRID 1630559Notes

Reaction equation

HRID 1630559 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C:9]([N:11]1[C:19]2[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[C:13]2[CH2:21][N:22]([CH3:25])[CH2:23][CH2:24][C:12]1=2)#[CH:10].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[CH3:25][N:22]1[CH2:23][CH2:24][C:12]2[N:11]([C:9]#[C:10][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=3)[C:19]3[CH:18]=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[C:13]=2[CH2:21]1

Participants

5

Reactant 3

HCID 5642162-Bromo-5-methylpyridineHCID 2724141Tetrabutylammonium FluorideHCID 594550005-Ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 68284376HCID 68284376, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-5-methyl-pyridine (250 mg, 1.45 mmol), 5-ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (391 mg, 1.74 mmol), TBAF.3H2O (1.374 g, 4.36 mmol) and dichloro bistriphenylphosphine palladium(II) (51 mg, 0.072 mmol) was stirred at 85° C. for 10 min. The reaction mixture was poured into water and extracted with EtOAc (3×100 mL). The organic layer was washed with water (3×100 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography (neutral alumina, eluent-0.5% MeOH in DCM) to yield 2,8-dimethyl-5-(5-methyl-pyridin-2-ylethynyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, freebase) δ (ppm): 8.41 (s, 1H), 7.5 (m, 2H), 7.4 (d, 1H), 7.18 (s, 1H), 7.08 (d, 1H), 3.6 (s, 2H), 3.0 (t, 2H), 2.83 (t, 2H), 2.58 (s, 3H), 2.42 (s, 3H), 2.37 (s, 3H).

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe organic layer was washed with water (3×100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (neutral alumina, eluent-0.5% MeOH in DCM)

Sources & evidence

ORD record
ord-a2f0d0c3b5654c7382bb83d7ba7bdb76
Source dataset
uspto-grants-2014_07
Patent number
US08791132B2

Reaction notes

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