Hydrogen Bromide → 2-Bromo-1-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-ethanone

HRID 400561Notes

Reaction equation

HRID 400561 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19](=[O:21])[CH3:20])[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[BrH:23].BrBr>C(O)(=O)C>[Br:23][CH2:20][C:19]([C:18]1[C:13]2[CH:12]=[CH:11][N:10]([S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:22])=[CH:6][CH:5]=3)(=[O:9])=[O:8])[C:14]=2[N:15]=[CH:16][N:17]=1)=[O:21]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 586917071-(7-Tosyl-7H-pyrrolo[2,3-D]pyrimidin-4-YL)ethan-1-one

Product 1

HCID 586917252-Bromo-1-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-ethanoneYield 56.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

[5.95 g, 18.88 mmol] of 1-[7-(Toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-ethanone was dissolved/suspended in 90 mL of glacial acetic acid and [7.53 mL, 10.197 g, 37.76 mmol] of 30% hydrogen bromide in acetic acid. Added dropwise to this stirring mixture at ambient temperature, was [0.970 mL, 3.02 g, 18.88 mmol] of bromine in 10 mL of glacial acetic acid over 1.0 hour. The reaction was stirred an additional 4.0 hours at ambient temperature during which time a yellow precipitate forms. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution. The organic phase was washed with water, brine, and dried with anhydrous sodium sulphate and the solvent was removed under reduce pressure. The crude solid was triturated/stirred with MTBE overnight and the solid isolated via suction filtration and airdried to yield 4.2 g of pale yellow solid, a 56.6% yield.

Workup

  1. additionAdded dropwise to this stirring mixture at ambient temperature
  2. customover 1.0 hour
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried with anhydrous sodium sulphate
  7. customthe solvent was removed
  8. stirringThe crude solid was triturated/stirred with MTBE overnight
  9. customthe solid isolated via suction filtration

Sources & evidence

ORD record
ord-594599694e6143f5a9104b223d61cf04
Source dataset
uspto-grants-2014_06
Patent number
US08741912B2

Reaction notes

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