Dichloromethane → HCID 66668399, compound

HRID 1186824Notes

Reaction equation

HRID 1186824 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17](I)=[C:12]2[CH:11]=[N:10]1.CC1(C)C(C)(C)[O:23][B:22](B2OC(C)(C)C(C)(C)O2)[O:21]1.C([O-])(=O)C.[K+].C(Cl)Cl>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17]([B:22]([OH:23])[OH:21])=[C:12]2[CH:11]=[N:10]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 66664841HCID 66664841, compound

Product 1

HCID 66668399HCID 66668399, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a 48 mL pressure bottle containing 1-(2-chloro-4-fluorophenyl)-4-iodo-1H-pyrazolo[3,4-b]pyridine (68.5 mg, 0.183 mmol) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (81.7 mg, 0.322 mmol), potassium acetate (85.1 mg, 0.867 mmol), and anhydrous DMSO (1 mL). The reaction mixture was purged with argon, then treated with PdCl2(dppf).CH2Cl2 (11.5 mg, 0.016 mmol). The reaction mixture was again purged with argon, securely capped, and heated to 85° C. for 1 h to give the desired intermediate. LC/MS (Condition B): ret. T=3.0 min, (M+H)+ 292.01.

Workup

  1. customThe reaction mixture was purged with argon
  2. additiontreated with PdCl2(dppf)
  3. customThe reaction mixture was again purged with argon
  4. customsecurely capped

Sources & evidence

ORD record
ord-e484cb013b804e8c801013f0ec4ea63c
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

Loading…