Sodium Iodide → HCID 86710246, compound

HRID 2405939Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[O:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[N:10]=2)[CH:3]=[N:2]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>[O:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:6]1[C:4]1[CH:5]=[N:1][N:2]([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])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-(1H-pyrazol-4-yl)-1,3-benzoxazole (0.250 g, 1.35 mmol) in acetonitrile (10 mL) was added cesium carbonate (1.10 g, 3.38 mmol, 2.5 eq), sodium iodide (0.041 g, 0.270 mmol, 0.2 eq) and (R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate (0.504 g, 1.76 mmol, 1.3 eq). The mixture was heated at 50° C. overnight. The reaction mixture 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 10-100% ethyl acetate/heptane to give ethyl (2R)-4-[4-(1,3-benzoxazol-2-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoate (0.482 g, 91% yield) as a white solid. LC-MS M+H+392.1.

Workup

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

Sources & evidence

ORD record: ord-bdca6c0533be49e0a97f1f9f2185c290
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809333B2

Reaction notes

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