Tetrabutylammonium Fluoride → HCID 59455029, compound

HRID 1401700Notes

Reaction equation

HRID 1401700 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[C:13]([N:15]1[C:23]2[CH:22]=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH:17]2[CH2:25][N:26]([CH3:29])[CH2:27][CH2:28][CH:16]12)#[CH:14].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>[CH3:29][N:26]1[CH2:27][CH2:28][C:16]2[N:15]([C:13]#[C:14][C:2]3[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=3)[C:23]3[CH:22]=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[C:17]=2[CH2:25]1

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 24694329Benzamide, 4-bromo-2-fluoro-N-methyl-HCID 68488962HCID 68488962, compound

Product 1

HCID 59455029HCID 59455029, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-2-fluoro-N-methyl-benzamide (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 (475 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 reduced pressure. The crude product obtained was purified by column chromatography using silica (100-200 mesh) and 0-2% MeOH:DCM as eluent. 1H NMR (CDCl3, free base) δ (ppm): 8.10 (t, 1H), 7.42 (d, 1H), 7.36 (d, 1H), 7.22 (d, 1H), 7.18 (m, 2H), 6.70 (bs, 1H), 3.95 (m, 2H), 3.20 (m, 4H), 3.05 (d, 3H), 2.80 (s, 3H), 2.42 (s, 3H).

Workup

  1. addition3H2O (475 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 reduced pressure

Sources & evidence

ORD record
ord-ea68473c80f8454fb550916a221537b9
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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