Tetrabutylammonium Fluoride → HCID 59803882, compound

HRID 253392Notes

Reaction equation

HRID 253392 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][O:7][C:8]2[C:33]([F:34])=[CH:32][C:11]([CH2:12][C:13]3[C:21]4[C:16](=[N:17][CH:18]=[CH:19][CH:20]=4)[N:15]([Si](C(C)C)(C(C)C)C(C)C)[CH:14]=3)=[C:10]([F:35])[CH:9]=2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[C:33]([F:34])=[CH:32][C:11]([CH2:12][C:13]3[C:21]4[C:16](=[N:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[C:10]([F:35])[CH:9]=2)=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59803883HCID 59803883, compound

Product 1

HCID 59803882HCID 59803882, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-[4-(4-chloro-benzyloxy)-2,5-difluoro-benzyl]-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (51, 0.150 g, 0.28 mmol) in tetrahydrofuran (10.0 mL) was added tetra-n-butylammonium fluoride (80.0 mg, 0.31 mmol). After 10 minutes, the reaction was concentrated and purified by silica gel column chromatography eluting with 50% ethyl acetate in hexane to give the compound as a white solid (P-1974, 30.8 mg, 28.9%). MS (ESI) [M+H+]+=385.3.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by silica gel column chromatography
  3. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-729b38089c2e43fe81b2af8c20a2856d
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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