Pyridine → HCID 57800487, compound

HRID 913393Notes

Reaction equation

HRID 913393 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([NH2:20])=O)[N:6]2[CH2:13][C:14]([F:17])([F:16])[F:15].N1C=CC=CC=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]#[N:20])[N:6]2[CH2:13][C:14]([F:16])([F:17])[F:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 24985459HCID 24985459, compound

Product 1

HCID 57800487HCID 57800487, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-5-cyano-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxamide (0.05 g, 0.17 mmol) in CH2Cl2 (6 mL) was added pyridine (0.104 g, 1.32 mmol), followed by dropwise addition of TFAA (0.14 g, 0.66 mmol). The mixture was stirred at rt for 4 h and then concentrated in vacuo. The residue was partitioned between EtOAc and 0.5N HCl. The organic phase was washed with 0.5N HCl and sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-50% EtOAc-hexanes gradient) and the product was crystallized from CH2Cl2-hexanes to afford the title compound as a white solid (0.033 g, 72% yield): MS (ES) m/z 284 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and 0.5N HCl
  3. washThe organic phase was washed with 0.5N HCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (0-50% EtOAc-hexanes gradient)
  7. customthe product was crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-a7218e52650f42f2a166c7281863379e
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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