Tetrahydrofuran → 6-fluoro-1H-indole-5-carboxylic acid

HRID 634298Notes

Reaction equation

HRID 634298 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[Si](C(C)C)(C(C)C)C(C)C)=[CH:4][C:3]=1[C:21]([OH:23])=[O:22].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOCC>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 115590896-fluoro-1-(triisopropylsilyl)-1H-indole-5-carboxylic acid

Product 1

HCID 114920336-fluoro-1H-indole-5-carboxylic acidYield 103.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-Fluoro-1-(triisopropylsilyl)-1H-indole-5-carboxylic acid (4.36 g, 13.00 mmol) was treated with THF (30 mL) and tetra-n-butylammonium fluoride (1.0 M in THF, 13.0 mL, 13.00 mmol) and stirred at RT for 15 min. The reaction mixture was diluted with Et2O (30 mL) resulting in a suspension which was collected by filtration affording 6-fluoro-1H-indole-5-carboxylic acid (2.41 g) as a white crystalline solid. MS (ESI, pos. ion) m/z: 180.1 (M+H)+. The crude material was used in the subsequent reaction without further purification.

Workup

  1. customresulting in a suspension which
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ebb4d035a7aa40af94828a1b9818ea92
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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