Potassium Carbonate → HCID 67134953, compound

HRID 1397853Notes

Reaction equation

HRID 1397853 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([CH:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([C:29]#[N:30])[CH:27]=3)[NH:22][CH:21]=2)[OH:19])[C:12]=1[F:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([C:29]#[N:30])[CH:27]=3)[NH:22][CH:21]=2)=[O:19])[C:12]=1[F:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 68432623HCID 68432623, compound

Product 1

HCID 67134953HCID 67134953, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a round bottom flask, {3-[(5-cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid benzyl ester (26, 3.79 g, 8.72 mmol), 20.00 mL of anhydrous tetrahydrofuran and Dess-Martin periodinane (4.44 g, 10.47 mmol) were added. The reaction mixture was stirred at room temperature for 1 hour, then poured into a mixture of 100 mL of 1 M potassium carbonate and 100 mL of 1 M sodium thiosulfate and extracted with 3×150 mL of ethyl acetate. The organic layers were combined and dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The residue was slurried in ether, filtered and the solids collected and dried to give the desired compound (27, 2.97 g, 79%).

Workup

  1. extractionextracted with 3×150 mL of ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. filtrationfiltered
  6. customthe solids collected
  7. customdried

Sources & evidence

ORD record
ord-201bb89e3f7d4375956c3fa3759b1856
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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