Trifluoroacetic acid → HCID 58405598, compound

HRID 44823Notes

Reaction equation

HRID 44823 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[CH:10][CH:9]=[N:8]1.C(O)(C(F)(F)F)=O.C1C(=O)N([I:33])C(=O)C1>C(#N)C>[I:33][C:10]1[CH:9]=[N:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:18])([CH3:17])[CH3:1])[C:11]=1[C:12]1[S:13][CH:14]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-Iodosuccinimide2×HCID 58405658HCID 58405658, compound

Product 1

HCID 58405598HCID 58405598, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring mixture of 2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)thiazole (Compound 2-BA-1) in 50 mL of acetonitrile at rt under nitrogen were added TFA (1 mL) and NIS (10.8 g). The reaction mixture was stirred at rt overnight and an additional amount of NIS (0.5 eq to 1.0 eq) was added as needed. The crude reaction mixture was slowly quenched with ˜30 mL of a saturated aqueous Na2S2O3 solution, and ˜30 mL of a saturated aqueous NaHCO3 solution. The reaction mixture was diluted with 50 mL of EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organic layer was purified by MPLC (eluted with 0-50% EtOAc/hex) to give 2-(4-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)thiazole (Compound 4-BA-1). LCMS: 408.0 m/z (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. customwas slowly quenched with ˜30 mL of a saturated aqueous Na2S2O3 solution, and ˜30 mL of a saturated aqueous NaHCO3 solution
  3. additionThe reaction mixture was diluted with 50 mL of EtOAc
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  6. customThe organic layer was purified by MPLC (eluted with 0-50% EtOAc/hex)

Sources & evidence

ORD record
ord-24decef880b34dd79d7cb6a3e58b87a3
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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