Tetrahydrofuran → [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-carbamic acid methyl ester

HRID 60082Notes

Reaction equation

HRID 60082 reaction equation
[CH3:1][O:2][C:3](=[O:25])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([CH:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[NH:16][CH:15]=2)[OH:13])[C:6]=1[F:24].O1CCCC1.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+]>[CH3:1][O:2][C:3](=[O:25])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Br:23])[CH:21]=3)[NH:16][CH:15]=2)=[O:13])[C:6]=1[F:24]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 159087TriacetoxyperiodinaneHCID 58368953{3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid methyl ester

Product 1

HCID 58087834[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-carbamic acid methyl esterYield 100.6%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

Into a reaction flask, {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid methyl ester (5, 1.91 g, 4.63 mmol) is combined with 10 mL of tetrahydrofuran and Dess-Martin periodinane (2.36 g, 5.56 mmol). The reaction is stirred at room temperature for 2 hours, then diluted with 50 mL of 1M aqueous potassium carbonate and 50 mL of 1M aqueous sodium thiosulfate and extracted with 3×30 mL of ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (6, 1.91 g).

Workup

  1. extractionextracted with 3×30 mL of ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-0c0928713c5349a9a363faa1ac6a5bd5
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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