Tetrahydrofuran → HCID 66832128, compound

HRID 58773Notes

Reaction equation

HRID 58773 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]2[C:28]([CH2:29][CH2:30][NH:31][C:32]([C:34]3[CH:38]=[C:37]([CH2:39][C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=4[F:47])[O:36][N:35]=3)=[O:33])=[C:27]([Si](CC)(CC)CC)[NH:26][C:23]2=[N:24][CH:25]=1.C1C[O:58]CC1>>[Cl:19][C:20]1[CH:21]=[C:22]2[C:28]([CH2:29][CH2:30][NH:31][C:32]([C:34]3[CH:38]=[C:37]([C:39](=[O:58])[C:40]4[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=4[F:47])[O:36][N:35]=3)=[O:33])=[CH:27][NH:26][C:23]2=[N:24][CH:25]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 66832015N-(2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide

Product 1

HCID 66832128HCID 66832128, compoundYield 22%

Procedure

A solution of tetrabutylammonium fluoride 1M in THF (1 mL; 1 mmol) was added to a solution of N-(2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide (0.105 g, 0.198 mmol) in THF (5 mL). The mixture was stirred overnight at room temperature and was evaporated. The residue was dissolved in dichloromethane, and the organic solution was washed with water and was concentrated under reduced pressure. The crude material was purified twice by flash chromatography on silica gel (eluent: 0 to 40% of ethyl acetate in dichloromethane) to give 0.019 g (22%) of N-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl)-5-(2,5-difluorobenzoyl)isoxazole-3-carboxamide as a white solid.

Workup

  1. customwas evaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe organic solution was washed with water
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude material was purified twice by flash chromatography on silica gel (eluent: 0 to 40% of ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-5cc08393b6654dfd95d5f247c4584ce9
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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