Tetrabutylammonium Fluoride → HCID 58086442, compound

HRID 1964927Notes

Reaction equation

HRID 1964927 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([CH:16]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=2)[OH:17])=[C:11]([F:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([CH:16]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[OH:17])=[C:11]([F:37])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58087876HCID 58087876, compound

Product 1

HCID 58086442HCID 58086442, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (4-Benzyloxy-2,5-difluoro-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (601, 1.00 g. 1.91 mmol) in tetrahydrofuran (15.0 mL) was added tetrabutylammonium fluoride, trihydrate (0.63 g, 2.04 mmol). The reaction was stirred at room temperature for 10 minutes. The reaction was roto-evaporated and purified with silica gel column chromatography eluting with 50% ethyl acetate in hexane to give the compound as a white solid (P-1902, 0.59 g, 84.0%). MS(ESI) [M+H+]+=367.4.

Workup

  1. customThe reaction was roto-evaporated
  2. custompurified with silica gel column chromatography
  3. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-388523c1a0764e639abc249228f0800b
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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