Trifluoroacetic acid → 2-(4-fluorophenyl)-5-(5-(2-hydroxyethyl)-6-(3-methyl-1H-indol-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595751Notes

Reaction equation

HRID 595751 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[N:32]=[C:31]([C:33]5[N:34](C(OC(C)(C)C)=O)[C:35]6[C:40]([C:41]=5[CH3:42])=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:30]([CH2:50][CH2:51][OH:52])=[CH:29][CH:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[CH:28]=[CH:29][C:30]([CH2:50][CH2:51][OH:52])=[C:31]([C:33]5[NH:34][C:35]6[C:40]([C:41]=5[CH3:42])=[CH:39][CH:38]=[CH:37][CH:36]=6)[N:32]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:14][CH3:15])=[O:16])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90333639tert-butyl 2-(6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-(2-hydroxyethyl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate

Product 1

HCID 903335002-(4-fluorophenyl)-5-(5-(2-hydroxyethyl)-6-(3-methyl-1H-indol-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-(2-hydroxyethyl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate (50 mg, 0.069 mmol) in CH2Cl2 (1.5 mL) was added TFA (1.5 mL). The resultant mixture was stirred at ambient temperature for 1.5 h then was concentrated in vacuo, diluted with EtOAc and washed successively with saturated NaHCO3 (aq) solution (1×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the title compound, which was used without further purification. MS (M+H): 627.

Workup

  1. concentrationthen was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed successively with saturated NaHCO3 (aq) solution (1×) and brine (1×)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2a5b2cdd1c6435d80fad367596ac007
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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