Boric Acid → 6-benzenesulfonyl-1H-indole

HRID 1475305Notes

Reaction equation

HRID 1475305 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[Si](C(C)C)(C(C)C)C(C)C)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].B(O)(O)O>C1COCC1.O>[C:1]1([S:7]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][NH:16]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 7628Boric AcidHCID 2724141Tetrabutylammonium FluorideHCID 867239396-Phenylsulfonyl-1-triisopropylsilanyl-1H-indole

Product 1

HCID 674423236-benzenesulfonyl-1H-indoleYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-phenylsulfonyl-1-triisopropylsilanyl-1H-indole 0.365 g, 0.88 mmol) in THF (10 mL) was added a solution of TBAF in THF (1 M, 1 mL) followed by a solution of boric acid (0.062 g, 1 mmol) in water (1 mL) and stirring was carried out for 2 h. The mixture was partitioned between water (50 mL) and DCM (3×30 mL) and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 0-40% EtOAc in petrol) gave the title compound (0.21 g) as a colourless solid. MS: [M+H]+=258.

Workup

  1. customThe mixture was partitioned between water (50 mL) and DCM (3×30 mL)
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give an oil
  5. washChromatography (SiO2; gradient elution with 0-40% EtOAc in petrol)

Sources & evidence

ORD record
ord-97e7d964af9848a38efabecb6b425699
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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