1-Bromo-2-methylpropane → HCID 67184255, compound

HRID 45893Notes

Reaction equation

HRID 45893 reaction equation
[CH2:1](Br)[CH:2]([CH3:4])[CH3:3].[Br:6][C:7]1[C:8]([C:12]2[C:13]([F:31])=[C:14]([NH:19][S:20]([C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[F:30])(=[O:22])=[O:21])[CH:15]=[CH:16][C:17]=2[F:18])=[N:9][NH:10][CH:11]=1>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Br:6][C:7]1[CH:11]=[N:10][N:9]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:8]=1[C:12]1[C:13]([F:31])=[C:14]([NH:19][S:20]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])(=[O:22])=[O:21])[CH:15]=[CH:16][C:17]=1[F:18]

Participants

6

Reactant 2

HCID 65551-Bromo-2-methylpropane2×HCID 178527518HCID 178527518, compound

Product 1

HCID 67184255HCID 67184255, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalyst2×HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To the residue, dissolved in dichloromethane (10 mL), isobutyl bromide (1 mL, 9 mmol) and tetrabutylammonium bromide (0.16 g, 0.5 mmol) in 7 N sodium hydroxide (10 mL) were added and the mixture was vigorously stirred at room temperature. After 2 h, only N-[3-(4-bromo-1H-pyrazol-3-yl)-2,4-difluorophenyl]-2,5-difluorobenzene-sulfonamide was present. Upon addition of more isobutyl bromide (3 mL, 27 mmol) and tetrabutylammonium bromide (0.45 g, 1.4 mmol) and after 18 h additional stirring the reaction was completed. The phases were separated and the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The crude residue was purified by flash chromatography (eluant: dichloromethane). First the regioisomer N-{3-[4-bromo-1-(2-methyl propyl)-1H-pyrazol-5-yl]-2,4-difluorophenyl}-2,5-difluoro-benzenesulfonamide (0.065 g, 0.13 mmol) was isolated, then the title product was obtained as a white solid (0.12 g, 0.2 mmol, 15% four steps).

Workup

  1. stirringafter 18 h additional stirring the reaction
  2. customThe phases were separated
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography (eluant: dichloromethane)

Sources & evidence

ORD record
ord-75c47ec92278458bbbfba38ee2478d81
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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