Bromine → HCID 59414580, compound

HRID 40833Notes

Reaction equation

HRID 40833 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]2=[N:7][CH:8]=1.[Br:24]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(=O)(O)[O-]>[Br:24][C:11]1[C:5]2[C:6](=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:22])[F:23])[CH:4]=2)[N:9]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:10]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 497590301-[(4-Methylphenyl)sulfonyl]-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59414580HCID 59414580, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 5-trifluoromethyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine (53.7 g, 158 mmol) in DCM (250 mL) was added a solution of bromine (16 mL, 316 mmol) in DCM (50 mL) dropwise. No significant exotherm was observed. After an hour at room temperature, the reaction mixture had thickened and stirring ceased. The reaction was deemed complete by tlc and was diluted with 1.2 litres of DCM and 50:50 saturated bicarbonate: saturated sodium thiosulfate aqueous solution. The organic layer was separated and further washed with the 50:50 aqueous mixture, dried over magnesium sulfate and evaporated. The crude yellow solid was triturated with diethyl ether and solid isolated and dried to give the product as a yellow powder (59 g, 59% yield)

Workup

  1. waitAfter an hour at room temperature
  2. customThe organic layer was separated
  3. washfurther washed with the 50:50 aqueous mixture
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude yellow solid was triturated with diethyl ether and solid
  7. customisolated
  8. customdried

Sources & evidence

ORD record
ord-4cfe9585defc4ed3b5cd4936863335ab
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Reaction notes

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