Dichloromethane → 1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

HRID 1186814Notes

Reaction equation

HRID 1186814 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=3)[N:9]=[CH:10][C:3]=12.CC1(C)C(C)(C)[O:25][B:24](B2OC(C)(C)C(C)(C)O2)[O:23]1.C([O-])(=O)C.[K+].C(Cl)Cl>CS(C)=O>[F:18][C:17]([F:20])([F:19])[C:16]1[C:11]([N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([B:24]([OH:25])[OH:23])=[C:3]3[CH:10]=[N:9]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 680582364-iodo-1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 680581751-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 48 mL pressure bottle containing Intermediate 73A (495 mg, 1.269 mmol) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (569 mg, 2.241 mmol), potassium acetate (571 mg, 5.82 mmol) and anhydrous DMSO (10 mL). The reaction mixture was purged with argon, treated with PdCl2(dppf).CH2Cl2 (56 mg, 0.077 mmol), and heated to 85° C. for 2 h 15 min to give conversion to the desired product. LC/MS (Condition B): ret. T=2.5 min, (M+H)+ 309.07.

Workup

  1. customThe reaction mixture was purged with argon
  2. additiontreated with PdCl2(dppf)

Sources & evidence

ORD record
ord-e8ffdf4b071f4266a7bc4408d543bba5
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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