Potassium Phosphate, Tribasic → 5-(4-Chloro-5-phenylphthalazin-1-yl)pyridin-3-amine

HRID 593697Notes

Reaction equation

HRID 593697 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.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]([NH2:33])[CH:30]=[N:31][CH:32]=2)O1.[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:27]2[CH:28]=[C:29]([NH2:33])[CH:30]=[N:31][CH:32]=2)=[N:3][N:4]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 438110685-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamineHCID 90424399N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamideHCID 904244121,4-Dichloro-5-phenylphthalazine

Product 1

HCID 904243545-(4-Chloro-5-phenylphthalazin-1-yl)pyridin-3-amineYield 66.2%

Reagents, catalysts & solvents 2

HCID 75806TricyclohexylphosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

5-(4-Chloro-5-phenylphthalazin-1-yl)pyridin-3-amine (0.800 g, 66.1% yield) was prepared from 1,4-dichloro-5-phenylphthalazine (1.00 g, 3.63 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (0.960 g, 4.36 mmol, commercial), K3PO4 (0.772 g, 3.63 mmol), Pd2(dba)3 (0.0330 g, 0.0360 mmol) and tricyclohexylphosphine (0.0200 g, 0.0730 mmol) by the methods described for the preparation of N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide in Example 1. The crude residue was taken to the next step without further purification. LCMS (Condition 11): retention time 0.86 min, [M+1]=333.1.

Workup

  1. customThe crude residue was taken to the next step without further purification

Sources & evidence

ORD record
ord-23122b1a6e224a6e8ac96201c209204b
Source dataset
uspto-grants-2016_01
Patent number
US09242966B2

Reaction notes

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