Potassium Phosphate, Tribasic → 4-Chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylphthalazine

HRID 593711Notes

Reaction equation

HRID 593711 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:18])=[N:4][N:3]=1.[CH3:19][C:20]1([CH3:40])[O:24][CH:23]([C:25]2[CH:26]=[N:27][CH:28]=[C:29](B3OC(C)(C)C(C)(C)O3)[CH:30]=2)[CH2:22][O:21]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(NS(C1C=NC=C(C2C3C(=C(C4C=CC=CC=4)C=CC=3)C(Cl)=NN=2)C=1)(=O)=O)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[Cl:18][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([C:29]2[CH:28]=[N:27][CH:26]=[C:25]([CH:23]3[CH2:22][O:21][C:20]([CH3:40])([CH3:19])[O:24]3)[CH:30]=2)=[N:3][N:4]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 903861763-(2,2-Dimethyl-1,3-dioxolan-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 90424399N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamideHCID 904244121,4-Dichloro-5-phenylphthalazine

Product 1

HCID 904245884-Chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5-phenylphthalazineYield 82.2%

Reagents, catalysts & solvents 2

HCID 75806TricyclohexylphosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

4-Chloro-1-(5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridin-3-yl)-5phenylphthalazine (1.00 g, 82.0% yield) was prepared from 1,4-dichloro-5-phenylphthalazine (0.800 g, 2.91 mmol), 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.887 g, 2.91 mmol), K3PO4 (0.617 g, 2.91 mmol), tricyclohexylphosphine (0.0160 g, 0.0580 mmol) and Pd2(dba)3 (0.0270 g, 0.0290 mmol) by the methods described for N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide in Example 1. The crude product was taken to next step without purification. LCMS (Condition 11): retention time 1.05 min, [M+1]=418.1.

Workup

  1. customThe crude product was taken to next step without purification

Sources & evidence

ORD record
ord-2dae4ecc3e564ea68cf63c3cec8030a5
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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