Trifluoroacetic acid → 5-(3-(ethylsulfonyl)phenyl)-8-methoxy-N,3-dimethyl-9H-pyrido[2,3-b]indol-7-amine

HRID 1642592Notes

Reaction equation

HRID 1642592 reaction equation
C(O[C:6]([N:8](C)[C:9]1[C:17]([O:18][CH3:19])=[C:16]2[C:12]([C:13]3[CH:30]=[C:29]([CH3:31])[CH:28]=[N:27][C:14]=3[N:15]2C(OC(C)(C)C)=O)=[C:11]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([S:38]([CH2:41][CH3:42])(=[O:40])=[O:39])[CH:33]=2)[CH:10]=1)=O)(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:41]([S:38]([C:34]1[CH:33]=[C:32]([C:11]2[CH:10]=[C:9]([NH:8][CH3:6])[C:17]([O:18][CH3:19])=[C:16]3[C:12]=2[C:13]2[CH:30]=[C:29]([CH3:31])[CH:28]=[N:27][C:14]=2[NH:15]3)[CH:37]=[CH:36][CH:35]=1)(=[O:40])=[O:39])[CH3:42]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 58880095tert-butyl 7-(tert-butoxycarbonyl(methyl)amino)-5-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indole-9-carboxylate

Product 1

HCID 588801275-(3-(ethylsulfonyl)phenyl)-8-methoxy-N,3-dimethyl-9H-pyrido[2,3-b]indol-7-amineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude residue from previous step (Compound 251) was dissolved in 3 mL CH2Cl2 and to were sequentially added 0.2 mL of anisole and 1 mL of TFA. The mixture was stirred at room temperature for 2 h. Solvent was removed in vacuum and the residue was basified with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and finally purified flash chromatography to furnish Compound 252 (287 mg, 70%, for 2 steps).

Workup

  1. customSolvent was removed in vacuum
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4 and finally purified flash chromatography

Sources & evidence

ORD record
ord-7fdbdb741c3042e699be4812b8dac51c
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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