Potassium Acetate → 1-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

HRID 1186803Notes

Reaction equation

HRID 1186803 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]([B:17]([OH:19])[OH:18])=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[F:20]C1C=C(F)C=CC=1N1C2=NC=CC(I)=C2C=N1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.C([O-])(=O)C.[K+]>CS(C)=O>[F:20][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N:8]1[C:12]2=[N:13][CH:14]=[CH:15][C:16]([B:17]([OH:19])[OH:18])=[C:11]2[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 666648441-(2,4-Difluorophenyl)-4-iodo-1H-pyrazolo[3,4-B]pyridineHCID 666684341-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

Product 1

HCID 666681771-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

Intermediate 63A was prepared according to the general procedure described in Intermediate 5A, except that the reaction mixture was heated at 85° C. for 75 min, using Intermediate 13A (100 mg, 0.280 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (133.1 mg, 0.524 mmol), potassium acetate (115.0 mg, 1.172 mmol), and DMSO (1.5 mL). The desired product was confirmed to be present by LC/MS (Condition B): 76%; ret. T=2.9 min; (M+H)+ 276.00.

Workup

  1. customIntermediate 63A was prepared
  2. customT=2.9 min

Sources & evidence

ORD record
ord-d9fed4139cd54650b392c1a3c1c48550
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

Loading…