Dichloromethane → HCID 66667969, compound

HRID 1186822Notes

Reaction equation

HRID 1186822 reaction equation
F[C:2]1[C:7](/[CH:8]=[N:9]/[NH:10][C:11]2[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][C:12]=2[F:19])=[C:6](I)[CH:5]=[CH:4][N:3]=1.IC1C=CN=C2N(C3C(F)=CC(F)=CC=3F)N=CC=12.CC1(C)C(C)(C)[O:44][B:43](B2OC(C)(C)C(C)(C)O2)[O:42]1.C([O-])(=O)C.[K+].C(Cl)Cl>CS(C)=O>[F:19][C:12]1[CH:13]=[C:14]([F:18])[CH:15]=[C:16]([F:17])[C:11]=1[N:10]1[C:2]2=[N:3][CH:4]=[CH:5][C:6]([B:43]([OH:44])[OH:42])=[C:7]2[CH:8]=[N:9]1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 68058238HCID 68058238, compoundHCID 87096087HCID 87096087, compound

Product 1

HCID 66667969HCID 66667969, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 48 mL pressure bottle containing (E)-2-fluoro-4-iodo-3-((2-(2,4,6-trifluorophenyl)hydrazono)methyl)pyridine (230 mg, 0.582 mmol), were added Intermediate 77A (133 mg, 0.355 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (330 mg, 1.30 mmol), potassium acetate (350 mg, 3.57 mmol), and anhydrous DMSO (8 mL). The reaction mixture was purged with argon, treated with PdCl2(dppf).CH2Cl2(64 mg, 0.087 mmol), and heated to 85° C. for 1.25 h to give the desired intermediate. LC/MS (Condition B): ret. T=2.9 min, (M+H)+ 294.03.

Workup

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

Sources & evidence

ORD record
ord-7fbb91ba790141d38ad591cb1033635d
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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