Tetrabutylammonium Fluoride → HCID 58213470, compound

HRID 340317Notes

Reaction equation

HRID 340317 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:25]=[CH:24][C:13]2=[C:14]3[C:19](=[C:20]([NH2:22])[N:21]=[C:12]2[CH:11]=1)[N:18]=[C:17]([Cl:23])[CH:16]=[CH:15]3)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:22][C:20]1[C:19]2[N:18]=[C:17]([Cl:23])[CH:16]=[CH:15][C:14]=2[C:13]2[CH:24]=[CH:25][C:10]([CH2:9][OH:8])=[CH:11][C:12]=2[N:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86652357HCID 86652357, compound

Product 1

HCID 58213470HCID 58213470, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-((tert-butyldimethylsilyloxy)methyl)-3-chlorobenzo[f][1,7]naphthyridin-5-amine (from the previous step) (1.0 eq.) and TBAF (1.1 eq.) in THF was stiffed at ambient temperature overnight. The reaction was quenched with saturated NaHCO3. The two phases were separated, and the aqueous layer was extracted twice with Et2O. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give (5-amino-3-chlorobenzo[f][1,7]naphthyridin-8-yl)methanol as a white solid.

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted twice with Et2O
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vacuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-495222593d854b53ab7218c868acc147
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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