Isopropyl iodide → HCID 90386218, compound

HRID 2170192Notes

Reaction equation

HRID 2170192 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.I[CH:18]([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[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][CH:18]([CH3:20])[CH3:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178449961HCID 178449961, compound

Product 1

HCID 90386218HCID 90386218, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N-(tert-butyl)-2-hydroxypyridine-3-sulfonamide (1.50 g, 4.85 mmol) in DMF (40 mL) was added 2-iodopropane (0.825 g, 4.85 mmol) followed by K2CO3 (1.34 g, 9.70 mmol) at RT. The reaction mixture was heated to 100° C. for 14 h. The reaction mixture was allowed to cool and the volatile components were removed under reduced pressure. The residue was diluted with cold water (150 mL) and extracted into ethyl acetate (2×100 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure and the residue was purified by CombiFlash (REDISEP®, silica gel, 24 g, 50% EtOAc/petroleum ether) to give 5-bromo-N-(tert-butyl)-2-isopropoxypyridine-3-sulfonamide (0.660 g, 37.7%) as a white solid. LCMS Condition B-22: retention time 1.92 min, [M+1]=351.0. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.13 (s, 9H), 1.35 (d, J=6.8 Hz, 6H), 5.06 (dt, J=13.6 Hz, J=6.8 Hz, 1H), 6.96 (s, 1H), 8.00 (d, J=2.6 Hz, 1H), 8.36 (d, J=2.6 Hz, 1H).

Workup

  1. temperatureto cool
  2. customthe volatile components were removed under reduced pressure
  3. additionThe residue was diluted with cold water (150 mL)
  4. extractionextracted into ethyl acetate (2×100 mL)
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customthe residue was purified by CombiFlash (REDISEP®, silica gel, 24 g, 50% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-09c3597fab894a79b9cdb7c8b04126e0
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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