Dichloromethane → 1-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

HRID 1186794Notes

Reaction equation

HRID 1186794 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16](I)=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)[O:22][B:21](B2OC(C)(C)C(C)(C)O2)[O:20]1.C([O-])(=O)C.[K+].C(Cl)Cl>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([B:21]([OH:22])[OH:20])=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 666684371-(4-Fluorophenyl)-4-iodo-1H-pyrazolo[3,4-B]pyridine

Product 1

HCID 666684341-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
84 °C

Procedure

To a 16×100 mm reaction vial was added Intermediate 2A (61.8 mg, 0.182 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (85.5 mg, 0.337 mmol), potassium acetate (77 mg, 0.785 mmol), and DMSO (1 mL). Argon was bubbled into the reaction mixture for 5 minutes. Next, PdCl2(dppf).CH2Cl2 (10 mg, 0.012 mmol) was added and the reaction mixture was heated at 84° C. for 18 h. The desired product was confirmed to be present by LC/MS (Condition B): 88.0%; ret. T=3.4 min; (M+H)+ 258.04.

Workup

  1. customTo a 16×100 mm reaction
  2. customArgon was bubbled into the reaction mixture for 5 minutes

Sources & evidence

ORD record
ord-54f09cdefddb4209adb9e59b972c0311
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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