Dichloromethane → HCID 68058275, compound

HRID 1186820Notes

Reaction equation

HRID 1186820 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([F:20])([F:19])[F:18])[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:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([B:24]([OH:25])[OH:23])=[C:3]2[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 666684764-iodo-1-(2-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 68058275HCID 68058275, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 48 mL pressure bottle containing Intermediate 76A (535 mg, 1.32 mmol) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (500 mg, 1.97 mmol), potassium acetate (520 mg, 5.30 mmol), and anhydrous DMSO (10 mL). The reaction mixture was flushed with argon, treated with PdCl2(dppf).CH2Cl2 (60 mg, 0.082 mmol), and heated to 105° C. for 1.25 h to give the desired product.

Workup

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

Sources & evidence

ORD record
ord-2fe5135967934fb1b077a1bd24ef8b4b
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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