Tetrabutylammonium Fluoride → HCID 59855195, compound

HRID 1435104Notes

Reaction equation

HRID 1435104 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:9]3[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[C:11]([O:18][Si](C(C)(C)C)(C)C)[CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:9]3[S:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[C:11]([OH:18])[CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57937503HCID 57937503, compound

Product 1

HCID 59855195HCID 59855195, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an alternative procedure, to a solution of methyl 5-(5-bromo-1H-benzimidazol-1-yl)-3-{[tert-butyl(dimethyl)-silyl]oxy}thiophene-2-carboxylate (12 g, 25 mmol) in 250 mL of THF cooled to 0° C. was added a 1M solution of tetrabutylammonium fluoride in THF (28 ml, 28 mmol). The reaction was quenched with water and extracted with EtOAc. The combined organic layers were washed with water, dried over MgSO4 and concentrated onto silica gel. The crude material was purified by flash column chromatography (0-5% MeOH/DCM) to give the title compound.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated onto silica gel
  6. customThe crude material was purified by flash column chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-d0919a764ddf4660ad0c293794c3bdeb
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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