Water → HCID 178420133, compound

HRID 1919694Notes

Reaction equation

HRID 1919694 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]3[NH:20][CH:19]=[N:18][N:17]=3)[C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:27]1([C:2]2[C:11]3[C:6](=[CH:7][N:8]=[CH:9][CH:10]=3)[C:5]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]4[NH:20][CH:19]=[N:18][N:17]=4)[C:4]=3[N:3]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 178478306HCID 178478306, compound

Product 1

HCID 178420133HCID 178420133, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To 5-chloro-7-(4H-1,2,4-triazol-3-yl)benzo[c][2,6]naphthyridine (21.3 mg), cesium carbonate (49 mg) and phenylboronic acid (19 mg) in dioxane (1 mL) was added PdCl2(dppf) under nitrogen atmosphere. The mixture stirred at 120° C. at 300 W (microwave) for 10 min. Water was added and residue obtained after extraction with dichloromethane was purified by preparative HPLC. LCMS (ES) m/z [M+1]+ 324.

Workup

  1. customresidue obtained
  2. extractionafter extraction with dichloromethane
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f237d34f07a74536b1eb625492d52d0e
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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