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

HRID 1036631Notes

Reaction equation

HRID 1036631 reaction equation
[Si]([O:8][CH2:9][CH2:10][C@@H:11]([NH:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[C:15]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:14]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>ClCCl>[F:37][C:34]1[CH:35]=[CH:36][C:31]([S:28]([NH:27][C@H:11]([CH2:10][CH2:9][OH:8])[CH2:12][N:13]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:14]2)(=[O:30])=[O:29])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86655913methyl [1-((2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(4-fluorophenyl)sulfonyl]amino}butyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

Product 1

HCID 86655914Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-hydroxybutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetateYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl [1-((2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(4-fluorophenyl)sulfonyl]amino}butyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate (1.2 g, 2.2 mmol) in dichloromethane (40 mL) was added 1 M TBAF (4.8 mL, 2.2 equiv.). After a period of 0.5 h the reaction mixture was quenched with 25% aqueous ammonium acetate, the organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified on combiflash (20% ethyl acetate in hexane to 100% ethyl acetate) to provide 849 mg of the title compound.

Workup

  1. customAfter a period of 0.5 h the reaction mixture was quenched with 25% aqueous ammonium acetate
  2. customthe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified on combiflash (20% ethyl acetate in hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-ae248ef9b2d04e1dbe424e31385a62a4
Source dataset
uspto-grants-2013_10
Patent number
US08546422B2

Reaction notes

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