4-Bromobenzenesulfonamide → HCID 68283979, compound

HRID 2408663Notes

Reaction equation

HRID 2408663 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:22]2[CH:21]=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[C:16]2[CH2:24][N:25]([CH3:28])[CH2:26][CH2:27][C:15]1=2)#[CH:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[CH3:28][N:25]1[CH2:26][CH2:27][C:15]2[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:22]3[CH:21]=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[C:16]=2[CH2:24]1

Participants

5

Reactant 3

HCID 696964-BromobenzenesulfonamideHCID 2724141Tetrabutylammonium FluorideHCID 594550005-Ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 68283979HCID 68283979, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromobenzenesulfonamide (200 mg, 0.84 mmol), 5-ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (391 mg, 1.0 mmol), TBAF.3H2O (793 mg, 2.5 mmol) and dichloro bis(triphenyl phosphine) palladium (II) (29 mg, 0.042 mmol) was stirred at 85° C. for 10 min. The reaction mixture was poured into water and extracted with EtOAc (3×50 mL). The organic layer was washed with water (3×100 mL), dried over anhydrous sodium sulfate and concentrated to afford crude material, which was purified by column chromatography using neutral alumina and 5% MeOH-DCM, followed by reverse phase HPLC to yield 4-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylethynyl)-benzenesulfonamide. 1H NMR (CD3OD, HCl salt) δ (ppm): 7.92 (d, 2H), 7.7 (d, 2H), 7.58 (d, 1H), 7.38 (s, 1H), 7.23 (d, 1H), 4.7 (d, 1H), 4.4 (d, 1H), 3.96 (m, 1H), 3.63 (m, 1H), 3.37 (m, 2H), 3.18 (s, 3H), 2.42 (s, 3H).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe organic layer was washed with water (3×100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto afford crude material, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6926ef209e7f4121a0611b73b32bfb19
Source dataset
uspto-grants-2014_08
Patent number
US08815843B2

Reaction notes

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