Sodium Iodide → HCID 86710244, compound

HRID 2405936Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[CH:15]=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:25][CH2:26][C@@:27]([CH3:37])([S:33]([CH3:36])(=[O:35])=[O:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C(#N)C>[CH3:37][C@@:27]([S:33]([CH3:36])(=[O:34])=[O:35])([CH2:26][CH2:25][N:1]1[CH:5]=[C:4]([C:6]2[CH:15]=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)[CH:3]=[N:2]1)[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(1H-pyrazol-4-yl)quinoxaline (0.400 g, 1.39 mmol) in acetonitrile (10 mL) was added cesium carbonate (8.73 g, 2.68 mmol, 2.5 eq), sodium iodide (0.032 g, 0.214 mmol, 0.2 eq) and (R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate (0.400 g 1.39 mmol, 1.3 eq). The reaction mixture was heated at 50° C. overnight. The reaction was filtered over a pad of diatomateous earth. The filtrate was evaporated and the crude was purified by flash chromatography on silica gel eluting with 40-100% ethyl acetate/heptane to give ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(quinoxalin-2-yl)-1H-pyrazol-1-yl]butanoate (0.078 g, 14% yield) as a colorless oil. LC-MS M+H+403.1.

Workup

filtrationThe reaction was filtered over a pad of diatomateous earth
customThe filtrate was evaporated
customthe crude was purified by flash chromatography on silica gel eluting with 40-100% ethyl acetate/heptane

Sources & evidence

ORD record: ord-8537ca90a6124d2e92100fad05960d26
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809333B2

Reaction notes

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