Sodium periodate → HCID 59437244, compound

HRID 244443Notes

Reaction equation

HRID 244443 reaction equation
[OH:1][CH:2](CO)[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:19]=[CH:18]3)([OH:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]1[C:31]#[N:32].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O>[O:1]=[CH:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[N:19]=[CH:18]3)([OH:14])[C:10]([F:12])([F:13])[F:11])[CH:6]=[C:5]1[C:31]#[N:32]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 59437202HCID 59437202, compound

Product 1

HCID 59437244HCID 59437244, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 242 mg (0.51 mmol) of 1-(2,3-dihydroxypropyl)-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carbonitrile in 6 mL of acetone and 3 mL of water was added 114 mg (0.53 mmol) of sodium periodate. After stirring overnight, the solids were filtered and rinsed with acetone. The acetone was then concentrated in vacuo and the residue was diluted with brine and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to afford 208 mg of 1-(2-oxoethyl)-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carbonitrile which was used without further purification.

Workup

  1. filtrationthe solids were filtered
  2. washrinsed with acetone
  3. concentrationThe acetone was then concentrated in vacuo
  4. additionthe residue was diluted with brine
  5. extractionextracted with EtOAc
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40543665890d434dbe46aa00fe5f7d9a
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

Loading…