Dichloromethane → HCID 66668207, compound

HRID 1186811Notes

Reaction equation

HRID 1186811 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[C:12]=3[F:19])[N:9]=[CH:10][C:3]=12.CC1(C)C(C)(C)[O:24][B:23](B2OC(C)(C)C(C)(C)O2)[O:22]1.C([O-])(=O)C.[K+].C(Cl)Cl>CS(C)=O>[F:19][C:12]1[C:13]([F:18])=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([B:23]([OH:24])[OH:22])=[C:3]2[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 66668290HCID 66668290, compound

Product 1

HCID 66668207HCID 66668207, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a 48 mL pressure bottle under N2 was added Intermediate 70A (169.2 mg, 0.451 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (217 mg, 0.855 mmol), potassium acetate (206 mg, 2.099 mmol) and anhydrous DMSO (4.5 mL). The reaction mixture was flushed with argon, then treated with PdCl2(dppf).CH2Cl2 (28.3 mg, 0.039 mmol). The reaction mixture was again flushed with argon, securely capped and heated at 85° C. for 1 h to give complete conversion to the desired product. LC/MS (Condition B): ret. T=3.3 min, (M+H)+ 294.03.

Workup

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

Sources & evidence

ORD record
ord-f391c265281a45ecb8d715706c40ecec
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

Loading…