Sodium methanesulfinate → HCID 10480864, compound

HRID 860988Notes

Reaction equation

HRID 860988 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[C:17]([C:25]([S:28]([CH3:31])(=[O:30])=[O:29])([CH3:27])[CH3:26])[CH:18]=[C:19]4[C:24]=3[N:23]=[CH:22][CH:21]=[CH:20]4)[CH:10]=2)=[CH:5][CH:4]=1.[CH3:32][S:33]([O-:35])=[O:34].[Na+]>CN(C=O)C.O>[CH3:32][S:33]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[C:17]([C:25]([S:28]([CH3:31])(=[O:30])=[O:29])([CH3:27])[CH3:26])[CH:18]=[C:19]4[C:24]=3[N:23]=[CH:22][CH:21]=[CH:20]4)[CH:10]=2)=[CH:5][CH:4]=1)(=[O:35])=[O:34]

Participants

5

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 69375565HCID 69375565, compound

Product 1

HCID 10480864HCID 10480864, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-(4′-Bromomethyl-biphenyl-3-yl)-6-(1-methanesulfonyl-1-methyl-ethyl)-quinoline (1.0 eq.) in DMF (0.1M) was added sodium methanesulfinate (1.3 eq.). The mixture was stirred at rt for 2 h, poured in water and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EA; 1:4) and stirring in EtOAc:Hex:Et2O (1:7:2) afforded the title compound as a white solid after filtration. 1H NMR (400 MHz, acetone-d6): δ 8.96 (dd, 1H), 8.49 (dd, 1H), 8.32 (d, 1H), 8.25 (d, 1H), 8.08 (t, 1H), 7.81–7.75 (m, 4H), 7.63–7.59 (m, 4H), 4.48 (s, 2H), 2.90 (s, 3H), 2.75 (s, 3H), 2.03 (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
  6. stirringFlash chromatography (Hex:EA; 1:4) and stirring in EtOAc

Sources & evidence

ORD record
ord-9bef664931c9425d8b7bdb291e6b9ad8
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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