3-Bromo-N,N-dimethylaniline → HCID 59455095, compound

HRID 1401701Notes

Reaction equation

HRID 1401701 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:11]([N:13]1[C:21]2[CH:20]=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH:15]2[CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][CH:14]12)#[CH:12].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:27][N:24]1[CH2:25][CH2:26][C:14]2[N:13]([C:11]#[C:12][C:2]3[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=3)[N:8]([CH3:10])[CH3:9])[C:21]3[CH:20]=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[C:15]=2[CH2:23]1

Participants

6

Reactant 3

HCID 1401023-Bromo-N,N-dimethylanilineHCID 2724141Tetrabutylammonium FluorideHCID 68488962HCID 68488962, compound

Product 1

HCID 59455095HCID 59455095, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

(3-Bromo-phenyl)-dimethylamine (100 mg, 0.5 mmol), 5-ethynyl-2,8-dimethyl-2,3,4,4a, 5,9b-hexahydro-1H-pyrido[4,3-b]indole (123 mg, 0.5 mmol), dichlorobis(triphenylphosphine)palladium(II) (17 mg, 0.25 mmol) and TBAF.3H2O (275 mg, 1.5 mmol) were mixed and stirred at 80° C. for 30 min under nitrogen. The progress of reaction was monitored by TLC and LCMS. The mixture was cooled to RT, water was added, and extracted with EtOAc. The organic layer was washed with water (1×10 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography using silica gel (100-200 mesh), neutralizing the silica gel with aq. Ammonia, and using 0-2% MeOH:DCM as eluent. 1H NMR (CDCl3, TFA salt) δ (ppm): 7.50 (d, 1H), 7.30 (m, 1H), 7.18 (d, 2H), 7.05 (d, 2H), 6.90 (m, 1H), 4.78 (m, 1H), 4.10 (m, 1H), 3.90 (m, 1H), 3.40 (m, 2H), 3.20 (m, 1H), 3.0 (s, 9H), 2.42 (s, 3H),

Workup

  1. addition3H2O (275 mg, 1.5 mmol) were mixed
  2. customThe progress of reaction
  3. temperatureThe mixture was cooled to RT
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water (1×10 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d99cb7c06f49412a8c7957366ba21564
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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