Sodium periodate → HCID 86664683, compound

HRID 1484737Notes

Reaction equation

HRID 1484737 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[C:10]([CH:19]=C)=[N:9]2)[CH:5]=[N:6][CH:7]=1.I([O-])(=O)(=O)=[O:22].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[C:10]([CH:19]=[O:22])=[N:9]2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67499984HCID 67499984, compound

Product 1

HCID 86664683HCID 86664683, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(1-(5-fluoropyridin-3-yl)-3-vinyl-1H-pyrazol-4-yl)isobutyramide (0.706 g, 2.57 mmol) in tetrahydrofuran (12.87 ml) and water (12.87 ml) was added osmium tetroxide (0.164 ml, 0.026 mmol). After 10 minutes at room temperature, sodium periodate (1.101 g, 5.15 mmol) was added in portions over 3 minutes and the resulting solution was stirred at room temperature. After 18 hours, the solution was poured into 10 mL water and was extracted with 3×10 mL dichloromethane. The combined organic layers were dried, concentrated and chromatographed (0-100% ethyl acetate/hexanes) to give N-(1-(5-fluoropyridin-3-yl)-3-formyl-1H-pyrazol-4-yl)isobutyramide (626 mg, 2.266 mmol, 88% yield) as a yellow solid: mp 140.0-142.0° C.; 1H NMR (300 MHz, CDCl3) δ 10.12 (s, 1H), 9.14 (s, 1H), 8.90 (d, J=2.0 Hz, 1H), 8.82 (s, 1H), 8.51 (d, J=2.5 Hz, 1H), 7.92 (dt, J=9.2, 2.4 Hz, 1H), 2.65 (dt, J=13.8, 6.9 Hz, 1H), 1.31 (d, J=6.9 Hz, 6H); ESIMS m/z 277 ([M+H]+).

Workup

  1. waitAfter 18 hours
  2. extractionwas extracted with 3×10 mL dichloromethane
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customchromatographed (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-79df2e3a8d5d422ab465c7bed116876f
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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