Tetrabutylammonium Fluoride → N-cyclohexyl-5-fluoro-N-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1696235Notes

Reaction equation

HRID 1696235 reaction equation
[CH:1]1([N:7]([CH3:28])[C:8]2[C:9]3[CH:17]=[CH:16][N:15]([Si](C(C)C)(C(C)C)C(C)C)[C:10]=3[N:11]=[CH:12][C:13]=2[F:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:1]1([N:7]([CH3:28])[C:8]2[C:9]3[CH:17]=[CH:16][NH:15][C:10]=3[N:11]=[CH:12][C:13]=2[F:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 67278086N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine

Product 1

HCID 67278116N-cyclohexyl-5-fluoro-N-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine (50 mL) in tetrahydrofuran (0.7 mL) was added tetra-n-butylammonium fluoride (0.372 mL, 1.0M in tetrahydrofuran) at ambient temperature. The reaction mixture was stirred at ambient temperature for 2 hours, then another 3 equivalent of tetra-n-butylammonium fluoride (0.372 mL) was added. The mixture was heated at 50° C. for 2 hours, at reflux for 6 hours. After cooling to ambient temperature, the mixture was concentrated. The residue was purified by column chromatography (gradient elution, n-hexane to 1:1 n-hexane/EtOAc) to give N-cyclohexyl-5-fluoro-N-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine (10 mg) as a pale yellow solid.

Workup

  1. temperatureThe mixture was heated at 50° C. for 2 hours
  2. temperatureat reflux for 6 hours
  3. temperatureAfter cooling to ambient temperature
  4. concentrationthe mixture was concentrated
  5. customThe residue was purified by column chromatography (gradient elution, n-hexane to 1:1 n-hexane/EtOAc)

Sources & evidence

ORD record
ord-d7cac9eb1ee74401a38ffb65366b2c0d
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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