Triisopropyl borate → 2-(6-Methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-boronic acid

HRID 902012Notes

Reaction equation

HRID 902012 reaction equation
Br[C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.C([Li])(C)(C)C.[B:23](OC(C)C)([O:28]C(C)C)[O:24]C(C)C>C1COCC1>[CH3:17][C:13]1[N:12]=[C:11]([C:3]2[C:2]([B:23]([OH:28])[OH:24])=[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][N:5]3[N:4]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 59700618HCID 59700618, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 597006142-(6-Methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-bromo-2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine (PREP. 17, 0.2 g, 0.69 mmol) in THF (10 mL) is cooled to −78° C. and treated with tert-butyllithium (1.7 M in pentane, 1.6 mL, 2.8 mmol). This solution is stirred for 30 minutes at −78° C., treated with triisopropyl borate (0.39 g, 2.08 mmol), and stirred for 2 hr at −78° C. The reaction is then quenched with 1N HCl and stirred for 30 minutes at room temp. Evaporation leads to the solid crude product that is used without further purification. MS ES+ m/e 253.9 (M+1).

Workup

  1. stirringstirred for 2 hr at −78° C
  2. customThe reaction is then quenched with 1N HCl
  3. stirringstirred for 30 minutes at room temp
  4. customEvaporation
  5. customis used without further purification

Sources & evidence

ORD record
ord-039820b98886424c90cfa49c471797a1
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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