Triacetoxyperiodinane → Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

HRID 1036632Notes

Reaction equation

HRID 1036632 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:28][CH2:29][OH:30])[CH2:13][N:14]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:28][CH:29]=[O:30])[CH2:13][N:14]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86655914Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-hydroxybutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

Product 1

HCID 86655915Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetateYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-hydroxybutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate (0.89 g, 1.9 mmol) in dichloromethane (16 mL) was added Dess-Martin reagent (0.99 g, 2.3 mmol, 1.2 equiv.). After a period of 45 min. the reaction mixture was purified directly by combiflash (20% ethyl acetate in hexane to 100% ethyl acetate) to give 697 mg of the title compound.

Workup

  1. customAfter a period of 45 min. the reaction mixture was purified directly by combiflash (20% ethyl acetate in hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-312c8876dc36485592127971fe0376ba
Source dataset
uspto-grants-2013_10
Patent number
US08546422B2

Reaction notes

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