1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 1-[5-fluoro-3-(3-fluoro-benzyl)-7-(1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanone

HRID 18195

Reaction equation

HRID 18195 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:26]=[CH:25][N:24]([Si](C(C)C)(C(C)C)C(C)C)[CH:23]=2)[C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[C:7]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)[C:6]=2[CH:21]=1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:26]=[CH:25][NH:24][CH:23]=2)[C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[C:7]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 593449101-[5-fluoro-3-(3-fluoro-benzyl)-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanone

Product 1

HCID 593448981-[5-fluoro-3-(3-fluoro-benzyl)-7-(1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanoneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[5-Fluoro-3-(3-fluoro-benzyl)-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanone (0.38 gm, 0.748 mmol) and tetrabutylammonium fluoride hydrate (0.28 gm, 0.89 mmol) were added to tetrahydrofuran (10 ml) and stirred at room temperature for four hours. The solution was concentrated under reduced pressure and purified by column chromatography to give 1-[5-fluoro-3-(3-fluoro-benzyl)-7-(1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanone (0.205 gm, 79% yield).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-ea46eb9885f64499b73736a5e2e99557
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Linked notes

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