1-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid → HCID 53679030, compound

HRID 376283Notes

Reaction equation

HRID 376283 reaction equation
C(=O)([O-])[O-].[Tl+2].[C:6]([O:10][C:11]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O)=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH3:21][Si:22]([CH3:44])([CH3:43])[CH2:23][CH2:24][O:25][CH2:26][O:27][CH2:28][C:29]1[N:34]=[C:33](OS(C(F)(F)F)(=O)=O)[CH:32]=[CH:31][CH:30]=1>C1C=CC=CC=1>[C:6]([O:10][C:11]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:28][O:27][CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:44])([CH3:43])[CH3:21])[N:34]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 10810259HCID 10810259, compoundHCID 178526101HCID 178526101, compound

Product 1

HCID 53679030HCID 53679030, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

9.68 g of thallium carbonate (20.6 mmol), 1 g of tetrakis(triphenylposphine)palladium (0.86 mmol) and 2.45 g of 1-tert-butoxycarbonylpyrrol-2-yl boronic acid (11.6 mmol) are added to a solution of 4 g of trifluoromethanesulfonic acid 6-(2-trimethylsilanyl-ethoxymethoxymethyl)pyridin-2-yl ester (10.3 mmol) and 40 ml of benzene degassed by bubbling of nitrogen. The mixture is stirred for 23 hours under an argon atmosphere. The insoluble matter is removed by filtration on celite and then the solution concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: dichloromethane/ethyl acetate; 99:1). 3.90 g of a yellow oil are recovered.

Workup

  1. customdegassed
  2. customby bubbling of nitrogen
  3. customThe insoluble matter is removed by filtration on celite
  4. concentrationthe solution concentrated under vacuum

Sources & evidence

ORD record
ord-2d8388ac3e0a49139d21ec0a00d678f4
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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