Trifluoroacetic acid → 2-Thiophenamine, 4-[1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-

HRID 2108748Notes

Reaction equation

HRID 2108748 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([C:20]2[CH:21]=[C:22]([NH:25]C(=O)OC(C)(C)C)[S:23][CH:24]=2)=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:7]1([CH3:8])[CH:6]=[CH:5][C:4]([S:1]([N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[C:13]([C:20]3[CH:21]=[C:22]([NH2:25])[S:23][CH:24]=3)=[CH:12]2)(=[O:3])=[O:2])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57633069Carbamic acid, [4-[1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-2-thienyl]-, 1,1-dimethylethyl ester (9CI)

Product 1

HCID 576330322-Thiophenamine, 4-[1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophen-2-ylcarbamate (120 mg, 0.26 mmol) was dissolved in 2 mL CH2Cl2, 2 mL TFA. After 15 minutes the reaction mixture was concentrated to an oil, dissolved in EtOAc, and washed with 0.1 NaOH. The organic layer was dried to a brown oil which was used as obtained.

Workup

  1. concentrationAfter 15 minutes the reaction mixture was concentrated to an oil
  2. dissolutiondissolved in EtOAc
  3. washwashed with 0.1 NaOH
  4. customThe organic layer was dried to a brown oil which
  5. customas obtained

Sources & evidence

ORD record
ord-87eb6376fd5f48e797626d5080cad636
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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