Triethylamine → HCID 86723266, compound

HRID 1846047Notes

Reaction equation

HRID 1846047 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:6])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]#[N:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 86723265HCID 86723265, compound

Product 1

HCID 86723266HCID 86723266, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-bromo-5-(ethylsulfonyl)benzamide (Preparation 74, 2.20 g, 7.53 mmol) in THF (50 mL) with triethylamine (1.57 mL, 11.3 mmol) was added trifluoroacetic anhydride (1.26 mg, 9.04 mmol) dropwise under nitrogen. The reaction was left to stir for 16 hours, before dilution with EtOAc (100 mL) and washing with sodium bicarbonate solution (saturated 100 mL), HCl (1M, 100 mL) and brine (100 mL). The organic phase was dried over MgSO4 and the solvent removed under reduced pressure to give the title compound as a colourless solid in 80% yield, 1.64 g.

Workup

  1. waitThe reaction was left
  2. washwashing with sodium bicarbonate solution (saturated 100 mL), HCl (1M, 100 mL) and brine (100 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-65ae34c3f0a448b4890aee77da8a076c
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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