2-Methyl-2-butene → HCID 58306778, compound

HRID 1909900Notes

Reaction equation

HRID 1909900 reaction equation
C([C:5]1[N:6]([C:18]([OH:20])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([Br:14])=[C:9]([Cl:15])[C:8]=2[CH:16]=[O:17])(C)(C)C.P([O-])(O)(O)=O.[Na+].[CH3:27][C:28](=[CH:30]C)[CH3:29].Cl([O-])=[O:33].[Na+]>O1CCOCC1.O>[Br:14][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([C:16]([OH:17])=[O:33])[C:9]=1[Cl:15])[N:6]([C:18]([O:20][C:28]([CH3:30])([CH3:29])[CH3:27])=[O:19])[CH:5]=[CH:13]2

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86654435HCID 86654435, compound

Product 1

HCID 58306778HCID 58306778, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of tert-butyl 5-bromo-6-chloro-7-formyl 1H-indole-1-carboxylic acid (2.9 g), sodium dihydrogen phosphate (2.0 g), 2-methyl-2-butene (2.6 g), water (10 mL), and 1,4-dioxane (30 mL) was added sodium chlorite (1.8 g) under ice-cooling. The reaction mixture was stirred under ice-cooling for 1 hour, and then at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added thereto, and a liquid-separation operation was carried out. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to obtain 5-bromo-1-(tert-butoxycarbonyl)-6-chloro-1H-indole-7-carboxylic acid (3.1 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and water
  4. additionwere added
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5838ba6c3b36434f9beaebb927aca6ad
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

Loading…