Triisopropyl borate → HCID 58913550, compound

HRID 1296941Notes

Reaction equation

HRID 1296941 reaction equation
COC1C=CC(C2C=NN(COCC[Si](C)(C)C)C=2C)=CC=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]([CH3:44])=[N:33][N:34]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[CH:35]=2)=[CH:27][CH:26]=1.[Li]CCCC.C([O:53][B:54](OC(C)C)[O:55]C(C)C)(C)C>C1COCC1>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]([CH3:44])=[N:33][N:34]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:42])([CH3:41])[CH3:43])[C:35]=2[B:54]([OH:55])[OH:53])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 21531Triisopropyl borateHCID 69380447HCID 69380447, compoundHCID 69380517HCID 69380517, compoundHCID 178418339Butyllithium

Product 1

HCID 58913550HCID 58913550, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(4-methoxy-phenyl)-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole and 4-(4-methoxy-phenyl)-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole (1 eq) was taken up in THF and cooled under nitrogen to −78° C. nBuLi (1.2 eq) was added dropwise and all was stirred for 30 minutes. Triisopropylborate (2.5 eq) was added and the reaction was stirred to room temperature. After 45 minutes, the reaction mixture was quenched with water and extracted with EtOAc. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a gum. This was purified by flash chromatography (9:1 hexane: EtOAc) to give 4-(4-methoxy-phenyl)-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole-5-boronic acid as an oil.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction was stirred to room temperature
  3. waitAfter 45 minutes
  4. customthe reaction mixture was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a gum
  10. customThis was purified by flash chromatography (9:1 hexane: EtOAc)

Sources & evidence

ORD record
ord-f15c6f580a194e448bf68c7a8710ea1f
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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