Dichloromethane → [6-Amino-5-(trifluoromethyl)pyridin-3-yl]boronic acid

HRID 2174944Notes

Reaction equation

HRID 2174944 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[B:13]1(B2OC(C)(C)C(C)(C)O2)[O:17]C(C)(C)C(C)(C)[O:14]1.C([O-])(=O)C.[K+].C(Cl)Cl>O1CCOCC1.C(OCC)(=O)C>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([B:13]([OH:17])[OH:14])=[CH:3][C:4]=1[C:9]([F:12])([F:11])[F:10]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 205253835-Bromo-3-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 53407570[6-Amino-5-(trifluoromethyl)pyridin-3-yl]boronic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

5-bromo-3-(trifluoromethyl)pyridin-2-amine (9.85 mmol, commercially available), Bis(pinacolato)diboron (11.82 mmol), potassium acetate (1.4 g) and (1,1-bis(diphenylphosphino)ferrocene)-dichloropalladium (II) complex with DCM (200 mg, commercially available) was dissolved in dioxane (75 mL) under argon atmosphere. The reaction mixture was refluxed for 8 h. The reaction mixture was cooled, diluted with ethyl acetate (75 mL) and filtered. The filtrate was concentrated. The crude product was purified over silica gel using 0-10% ethyl acetate in petroleum ether to obtain the titled boronic acid derivative.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was purified over silica gel using 0-10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e4a56016496947f6bacc45c5abcb4431
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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