Triethyloxonium tetrafluoroborate → 2-Ethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole

HRID 1973027Notes

Reaction equation

HRID 1973027 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)[O:3]1.F[B-](F)(F)F.[CH2:24]([O+](CC)CC)[CH3:25]>C(OCC)(=O)C>[CH2:24]([N:14]1[CH:13]=[C:12]2[C:16]([CH:17]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:18])([CH3:1])[O:3]3)[CH:10]=[CH:11]2)=[N:15]1)[CH3:25]

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 441192506-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

Product 1

HCID 585298202-Ethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (0.63 g, 2.56 mmol) in ethyl acetate (7.5 mL) was added triethyloxonium tetrafluoroborate (0.65 g, 3.33 mmol). The mixture was stirred at rt for 5 h under nitrogen (turned to a white suspension after about 0.5 h). The mixture was diluted with ethyl acetate (50 mL) and washed with saturated, aqueous sodium bicarbonate (50 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL), the combined organic layers were dried over MgSO4, filtered and concentrated. The crude purified using an ISCO® instrument using 0-40% ethyl acetate in hexanes. LC-MS [M+H]+=2732, RT=3.27 min.

Workup

  1. waitturned to a white suspension after about 0.5 h
  2. washwashed with saturated, aqueous sodium bicarbonate (50 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude purified

Sources & evidence

ORD record
ord-6017c01c82dd4f25a902b0567a0dcfbb
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

Loading…