Sodium Iodide → HCID 90046968, compound

HRID 1504998Notes

Reaction equation

HRID 1504998 reaction equation
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[OH:18])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:19])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:27][C:28]([CH3:31])([OH:30])[CH3:29].[I-].[Na+].CC1(C)CO1>CN(C=O)C>[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:27][C:28]([CH3:31])([OH:30])[CH3:29])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:19])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 684091-Chloro-2-methylpropan-2-olHCID 136628985HCID 136628985, compound

Product 1

HCID 90046968HCID 90046968, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(tert-butylsulfonyl)-4-chloroquinolin-7-ol (250 mg, 0.834 mmol) in DMF (2756 μl) was added K2CO3 (576 mg, 4.17 mmol) followed by 1-chloro-2-methylpropan-2-ol (209 μl, 2.502 mmol). After 10 min, LCMS showed no product. Heated reaction to 60° C. No reaction after 3 hr at this temperature. Added sodium iodide (375 mg, 2.50 mmol) and 2,2-dimethyloxirane (371 μl, 4.17 mmol) and stirred for 2 days at to 60° C. The crude sample was purified via Biotage normal phase chromatography (25 g SNAP column, 0% -80%, 80%. hex/EtOAc). The pure product containing-fractions were combined and concentrated leading to the product as an off-white solid: 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)-2-methylpropan-2-ol (46 mg, 0.124 mmol, 14.83% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (s, 6H) 1.33 (s, 9H) 4.03 (s, 2H) 4.56 (s, 1H) 7.72 (s, 1H) 7.76 (d, J=4.80 Hz, 1H) 8.64 (s, 1H) 8.94 (d, J=4.80 Hz, 1H). MS (m/z) 372.2 (M+H+).

Workup

  1. temperatureHeated
  2. customreaction to 60° C
  3. customNo reaction after 3 hr at this temperature
  4. customThe crude sample was purified via Biotage normal phase chromatography (25 g SNAP column, 0% -80%, 80%. hex/EtOAc)
  5. additionThe pure product containing-fractions
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f9d670ca730a4916aa8b3fd89a904414
Source dataset
uspto-grants-2015_12
Patent number
US09216965B2

Reaction notes

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