Potassium Carbonate → (1-((Pivaloyloxy)methyl)-1H-indazol-4-yl)boronic acid

HRID 246608Notes

Reaction equation

HRID 246608 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([B:10]([OH:12])[OH:11])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[C:13]([O:19][CH2:20]Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:13]([O:19][CH2:20][N:1]1[C:9]2[C:4](=[C:5]([B:10]([OH:12])[OH:11])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 441183101H-Indazole-4-boronic acid

Product 1

HCID 71279678(1-((Pivaloyloxy)methyl)-1H-indazol-4-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 1H-indazol-4-ylboronic acid (0.2 g, 1.227 mmol), chloromethyl pivalate (554 mg, 3.68 mmol) and K2CO3 (509 mg, 3.68 mmol) in dry DMF (10 mL) was heated to 30° C. for 16 hours. Reaction was quenched with water and product extracted with ethyl acetate (150 mL), then washed with water (3×20 mL) and brine (2×20 mL), then dried over Na2SO4, filtered and concentrated. The product (114 mg, crude) was obtained and used into next step without further purification. LCMS: (M+Na)+=299.

Workup

  1. customReaction
  2. customwas quenched with water and product
  3. extractionextracted with ethyl acetate (150 mL)
  4. washwashed with water (3×20 mL) and brine (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product (114 mg, crude) was obtained
  9. customused into next step without further purification

Sources & evidence

ORD record
ord-59ea6838107e4f3a887081ff9ccff2ef
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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