Tetrahydrofuran → HCID 59377733, compound

HRID 1691824Notes

Reaction equation

HRID 1691824 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][CH2:11][Si](C(C)(C)C)(C)C)=[CH:4][C:3]=1[NH:19][C:20]([N:22]1[CH:27]=[CH:26][C:25](=[O:28])[CH2:24][C@H:23]1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:21].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1C[O:57]CC1>>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][CH2:11][OH:57])=[CH:4][C:3]=1[NH:19][C:20]([N:22]1[CH:27]=[CH:26][C:25](=[O:28])[CH2:24][C@H:23]1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:21]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 66908018HCID 66908018, compound

Product 1

HCID 59377733HCID 59377733, compound

Procedure

To a solution of (S)-2-(4-Fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid {2-bromo-5-[2-(tert-butyl-dimethyl-silanyl)-ethoxy]-4-chloro-phenyl}-amide (0.095 g, 0.158 mmol) in THF (5 ml) was added 1.0 M TBAF in THF (0.35 ml, 0.348 mmol). The mixture was stirred at room temperature for three hours. Buffer (pH 2) was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/1:1) gave (S)-2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid [2-bromo-4-chloro-5-(2-hydroxy-ethoxy)-phenyl]-amide (0.198 g) as a white foam. MS (M+H) 484.

Workup

  1. additionBuffer (pH 2) was added
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the residue by flash chromatography (hex:EtOAc/1:1)

Sources & evidence

ORD record
ord-420994ab6121450aa0342329064ae173
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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