Methanol → HCID 10073897, compound

HRID 860985Notes

Reaction equation

HRID 860985 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26](SC)[N:25]=4)[CH:19]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=O)=[O:3].CO.[C:34]([O-])(O)=O.[Na+].O[O:40][S:41]([O-:43])=O.[K+].[OH2:45]>C1COCC1>[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([S:41]([CH3:34])(=[O:43])=[O:40])[N:25]=4)[CH:19]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:3])=[O:45]

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 69373347HCID 69373347, compound

Product 1

HCID 10073897HCID 10073897, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(1-methanesulfonyl-1-methyl-ethyl)-8-[3-(6-methylsulfanyl-pyridin-2-yl)-phenyl]-quinoline from Step 2 (1.0 eq.) in THF:MeOH: saturated aqueous NaHCO3 (2:1:1) was added Oxone (2.2 eq.). The mixture was stirred for 12 h at rt, poured in water and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Tol:Ace; 4:1) afforded the title compound as a white solid. 1H NMR (500 MHz, acetone-d6): δ 8.93 (dd, 1H), 8.55 (t, 1H), 8.46 (dd, 1H), 8.30–8.20 (m, 5H), 7.99 (dd, 1H), 7.89 (dt, 1H), 7.65 (t, 1H), 7.57 (dd, 1H), 3.33 (s, 3H), 2.74 (s, 3H), 2.00 (s, 6H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d2c4897db004cbea02d06a0be4c3c07
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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