Water → HCID 58086595, compound

HRID 1261154Notes

Reaction equation

HRID 1261154 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:32])=[C:11]([C:28]([F:31])=[CH:29][CH:30]=1)[CH2:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:20]=2)[NH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:35]([Si:38](Cl)([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])([CH3:37])[CH3:36].O>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([F:32])=[C:11]([C:28]([F:31])=[CH:29][CH:30]=1)[CH2:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:20]=2)[N:15]([Si:38]([CH:42]([CH3:44])[CH3:43])([CH:39]([CH3:41])[CH3:40])[CH:35]([CH3:37])[CH3:36])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 58087154HCID 58087154, compound

Product 1

HCID 58086595HCID 58086595, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-(3-Benzyloxy-2,6-difluoro-benzyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (P-1455, 700.0 mg, 1.64 mmol, prepared as described in Example 24, Scheme 43a) in tetrahydrofuran (40.0 mL) was added sodium hydride (60% in mineral oil, 100.0 mg, 2.5 mmol). After 10 minutes, triisopropylsilyl chloride (0.60 mL, 0.0028 mol) was added to the reaction. The reaction was stirred at room temperature for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the compound as colorless oil (548, 0.85 g, 89%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-519328e21d3245378d7209528755e64d
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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