m-Chloroperbenzoic acid → 3-Bromo-5-(5-fluoroindoline-1-carbonyl)-pyridine-1-oxide

HRID 74592Notes

Reaction equation

HRID 74592 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15]([C:19]([N:21]2[C:29]3[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)=[O:20])[CH:16]=[N:17][CH:18]=1>C(Cl)Cl>[Br:12][C:13]1[CH:18]=[N+:17]([O-:9])[CH:16]=[C:15]([C:19]([N:21]2[C:29]3[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)=[O:20])[CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 58386567HCID 58386567, compound

Product 1

HCID 673382653-Bromo-5-(5-fluoroindoline-1-carbonyl)-pyridine-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.19 g (1.1 mmol) m-chloroperbenzoic acid were added to 0.32 g (0.98 mmol) (5-bromo-pyridin-3-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone in 5.0 mL DCM and the mixture was stirred for 4 h at RT. In addition, a further 95 mg (0.55 mmol) m-chloroperbenzoic acid were added to the reaction mixture and it was stirred for 48 h at RT. Then the reaction mixture was diluted with DCM and extracted with 1N aqueous sodium hydroxide solution. The organic phase was dried on sodium sulphate, evaporated down and dried under HV.

Workup

  1. stirringwas stirred for 48 h at RT
  2. extractionextracted with 1N aqueous sodium hydroxide solution
  3. customThe organic phase was dried on sodium sulphate
  4. customevaporated down
  5. customdried under HV

Sources & evidence

ORD record
ord-473eb45c905b456aafcd30c6175fe728
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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