Trifluoroacetic anhydride → HCID 57744887, compound

HRID 1661492Notes

Reaction equation

HRID 1661492 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=O)=[C:4]([NH:11][C:12](=[O:17])[C:13](F)(F)F)[C:3]=1[CH3:18].[CH3:19]CN(C(C)C)C(C)C.NC1C(C)=C(Br)SC=1C(OC)=O.[C:40]([O:46][C:47]([C:49](F)(F)F)=O)(C(F)(F)F)=[O:41]>C(Cl)Cl.C(Cl)(Cl)Cl>[Br:1][C:2]1[S:6][C:5]2[C:7]([OH:9])=[C:13]([C:40]([O:46][CH2:47][CH3:49])=[O:41])[C:12](=[O:17])[N:11]([CH3:19])[C:4]=2[C:3]=1[CH3:18]

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 67429515HCID 67429515, compoundHCID 86617314HCID 86617314, compound

Product 1

HCID 57744887HCID 57744887, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 5-bromo-4-methyl-3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate. At 0° C., DIEA (4.32 mL, 24.8 mmol) was added dropwise to a solution of methyl 3-amino-5-bromo-4-methylthiophene-2-carboxylate (6.20 g, 24.8 mmol) in DCM (100 mL), followed by dropwise addition of TFAA (3.45 mL, 24.8 mmol). The mixture was stirred at room temperature for 18 hours, diluted with CHCl3, washed with water, dried over MgSO4, and evaporated. The crude product was purified by flash chromatography using EtOAc/hexanes to give the title compound. MS (ESI) m/z: Calculated; 346.1: Observed; 345.9. 1H NMR (300 MHz, CDCl3) δ ppm 9.62 (1H, br. s.), 3.89 (3H, s), 2.15 (3H, m).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-f0067b49f5f34eaea57d9a9d18ff9677
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

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