Potassium Carbonate → HCID 90386297, compound

HRID 2170163Notes

Reaction equation

HRID 2170163 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:10])=[O:11])[C:5]([O:8][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178449961HCID 178449961, compound

Product 1

HCID 90386297HCID 90386297, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N-(tert-butyl)-2-hydroxypyridine-3-sulfonamide (2.00 g, 6.47 mmol) in DMF (40 mL) was added 4-methoxybenzyl chloride (1.76 mL, 12.9 mmol) followed by K2CO3 (1.78 g, 12.9 mmol) at ambient temperature. The reaction mixture was heated to 100° C. for 14 h, diluted with cold water (100 mL). The aqueous mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give a residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 50% EtOAc/hexanes) to obtain 5-bromo-N-(tert-butyl)-2-((4-methoxybenzyl)oxy)pyridine-3-sulfonamide (1.50 g, 54.0%). LCMS Condition B-39: retention time 2.53 min, [M+1]=429.0. 1H NMR (400 MHz, CDCl3) 1.25 (s, 9H), 3.81 (s, 3H), 6.88-6.91 (m, 2H), 7.24-7.30 (m, 4H), 7.55 (d, J=2.8 Hz, 1H), 8.11 (d, J=2.8 Hz, 1H).

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-130847b153594d47aeb438f55a38bfe9
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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