Water → 3-{[6-(Propan-2-yl)pyridin-3-yl]methyl}-1H-pyrrolo[2,3-b]pyridine

HRID 1952020Notes

Reaction equation

HRID 1952020 reaction equation
[CH:1]([C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([Si](C(C)C)(C(C)C)C(C)C)[CH:12]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH:1]([C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 595932813-(6-Isopropyl-pyridin-3-ylmethyl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 159823433-{[6-(Propan-2-yl)pyridin-3-yl]methyl}-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To 3-(6-Isopropyl-pyridin-3-ylmethyl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (39, 35.0 mg, 0.086 mmol) in tetrahydrofuran (3.0 mL) was added tetra-n-butylammonium fluoride (29 mg, 0.11 mmol). The reaction was stirred at 20° C. for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 10% methanol in dichloromethane to give compound (P-0019, 18.0 mg, 81.9%). MS (ESI) [M+H+]+=252.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 10% methanol in dichloromethane
  7. customto give compound (P-0019, 18.0 mg, 81.9%)

Sources & evidence

ORD record
ord-38e97ec1ff7146ef83c12955728ce276
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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