4-Bromobenzenesulfonamide → HCID 71007593, compound

HRID 2408665Notes

Reaction equation

HRID 2408665 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]([N:14]1[C:26]2[CH2:25][N:24]([CH3:27])[CH2:23][CH2:22][C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[C:18]([CH3:28])[CH:19]=2)#[CH:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O>[CH3:27][N:24]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:28])[CH:19]=3)[N:14]([C:12]#[C:13][C:2]3[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=3)[C:26]=2[CH2:25]1

Participants

6

Reactant 3

HCID 696964-BromobenzenesulfonamideHCID 2724141Tetrabutylammonium FluorideHCID 71268725HCID 71268725, compound

Product 1

HCID 71007593HCID 71007593, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-bromo-benzenesulfonamide (200 mg, 0.84 mmol), 9-ethynyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-β-carboline (228 mg, 1.01 mmol), TBAF.3H2O (801 mg, 2.54 mmol) and dichloro bis(triphenylphosphine) palladium(II) (30 mg, 0.042 mmol) was stirred at 85° C. for 10 min. The reaction mixture was poured into water and extracted with EtOAc (3×25 mL). The organic layer was washed with water (3×30 mL), dried over anhydrous sodium sulfate and evaporated to afford crude material, which was purified by reverse phase HPLC to yield 4-(2,6-dimethyl-1,2,3,4-tetrahydro-β-carbolin-9-ylethynyl)-benzenesulfonamide. 1H NMR (CDCl3, freebase) δ (ppm): 7.9 (d, 2H), 7.6 (d, 2H), 7.4 (d, 1H), 7.3 (s, 1H), 7.1 (d, 1H), 3.78 (s, 2H), 2.82 (t, 2H), 2.79 (t, 2H), 2.6 (s, 3H), 2.42 (s, 3H).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe organic layer was washed with water (3×30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto afford crude material, which
  6. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-28b04eb5d55e463eaf8bacb1bdd99611
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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