Sodium Iodide → HCID 70856732, compound

HRID 2405946Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:24][CH2:25][C@@:26]([CH3:36])([S:32]([CH3:35])(=[O:34])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(#N)C>[CH3:36][C@@:26]([S:32]([CH3:35])(=[O:33])=[O:34])([CH2:25][CH2:24][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.8 g, 4.12 mmol) in acetonitrile (10 mL) was added cesium carbonate (3.36 g, 10.3 mmol, 2.5 eq), sodium iodide (0.124 g, 0.825 mmol, 0.2 eq) and (R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate (1.54 g, 5.36 mmol, 1.3 eq). The mixture was heated at 50° C. overnight. The reaction mixture was filtered over a pad of diatomateous earth and the filtrate was evaporated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10-100% ethyl acetate/heptane to give ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate (0.810 g, 49% yield) as a white solid. LC-MS M+H+401.3.

Workup

filtrationThe reaction mixture was filtered over a pad of diatomateous earth
customthe filtrate was evaporated to dryness
customThe crude product was purified by flash chromatography on silica gel eluting with 10-100% ethyl acetate/heptane

Sources & evidence

ORD record: ord-1c9378bde2a9424fb689e6d12931c92c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809333B2

Reaction notes

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