Potassium Phosphate, Tribasic → HCID 57799797, compound

HRID 2101185Notes

Reaction equation

HRID 2101185 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[N:3]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>Cl[Pd]Cl.O1CCOCC1.O>[CH:21]1([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=3)[CH:5]=[C:4]([NH:14][C:15]3[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=3)[N:3]=2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2760897Cyclopropylboronic acidHCID 57799674(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine

Product 1

HCID 57799797HCID 57799797, compoundYield 0.8%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
130 °C

Procedure

To a mixture of (1-Chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (0.2887 g 1 mmol), cyclopropyl boronic acid (0.1718 g, 2 mmol), PdCl2 (0.0177 g, 10% mmol), and K3PO4 (0.5307 g, 2.5 mmol) under Argon was added Dioxane/H2O=10:1(1 ml) and P(tBu)3 (20% mmol). The mixture was heated to 130° C. and stirred overnight. The product was purified by preparative HPLC to give 2.5 mg of solid. LC-MS: m/e 295 (MH+).

Workup

  1. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c0b83d7aca5b4d6294df95c8b3aa03e9
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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