Sodium Hydroxide → HCID 86704204, compound

HRID 1497662Notes

Reaction equation

HRID 1497662 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([N:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[N:23]=[C:24]([CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[S:25][CH:26]=2)[C:17]=1[F:33])[CH2:13][O:14][CH3:15])(=[O:11])=[O:10].C([O-])(=O)C.[Na+].[Br:39]Br.[OH-].[Na+]>C(O)(=O)C>[Br:39][C:26]1[S:25][C:24]([CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[N:23][C:22]=1[C:18]1[C:17]([F:33])=[C:16]([N:12]([CH2:13][O:14][CH3:15])[S:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])(=[O:10])=[O:11])[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 517045Sodium AcetateHCID 131734223HCID 131734223, compound

Product 1

HCID 86704204HCID 86704204, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,5-difluoro-N-{2-fluoro-3-[2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]phenyl}-N-(methoxymethyl)benzenesulfonamide (1.4 g, 2.808 mmol) was dissolved in acetic acid (28 mL), sodium acetate (461 mg, 5.616 mmol, 2 eq) was added and the mixture was stirred until complete dissolution. Bromine (0.2 mL, 3.9 mmol, 1.4 eq) was then added dropwise over 45 min and stirred at r.t. overnight. The reaction mixture was then added dropwise to a cooled 1 N solution of sodium hydroxide (300 mL) and the mixture was extracted with ethyl acetate. The organic phase was washed with 0.5 N sodium hydroxide, 5% NaHSO3 and brine, dried over Na2SO4 and evaporated to dryness, affording 1.26 g (78%) of the title product as colourless oil.

Workup

  1. stirringstirred at r.t. overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with 0.5 N sodium hydroxide, 5% NaHSO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e3c6144257fd4af59790df4fbfcc8029
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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