Dichloromethane → HCID 68058495, compound

HRID 1186818Notes

Reaction equation

HRID 1186818 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17](I)=[C:12]3[CH:11]=[N:10]2)[CH:5]=[C:6]([F:8])[CH:7]=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:3]=[C:4]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([B:22]([OH:23])[OH:21])=[C:12]3[CH:11]=[N:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 68058174HCID 68058174, compound

Product 1

HCID 68058495HCID 68058495, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a 48 mL pressure bottle containing Intermediate 75A (558.6 mg, 1.46 mmol) was added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (569.2 mg, 2.24 mmol), potassium acetate (584.3 mg, 5.95 mmol), and anhydrous DMSO (11 mL). The reaction mixture was flushed with argon and treated with PdCl2(dppf).CH2Cl2 (59.1 mg, 0.081 mmol). The reaction mixture was heated to 85° C. for 1 h and then at 105° C. for 1.5 h to give conversion to the desired product. LC/MS (Condition B): ret. T=4.29 min, (M+H)+ 291.99, 292.99.

Workup

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

Sources & evidence

ORD record
ord-bf43cf5635e94e5fb9dceec48f5abb6a
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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