Water → 8-(Pyridin-4-yl)-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one

HRID 920921Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[C:25](=[O:27])[N:24]([CH2:28][CH2:29][C:30]1[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=1)[N:23]=[CH:22]2.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]>[N:1]1[CH:6]=[CH:5][C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[C:25](=[O:27])[N:24]([CH2:28][CH2:29][C:30]2[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=2)[N:23]=[CH:22]3)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A reaction tube was charged with pyridin-4-ylboronic acid (0.223 mmol), K2CO3 (61.7 mg, 0.447 mmol) under a dry nitrogen atmosphere. A solution of 8-chloro-2-(2-quinolin-2-yl-ethyl)-2H-phthalazin-1-one (50 mg, 0.186 mmol) in 1,4-dioxane (5 mL) along with PdCl2(dppf) (5.45 mg, 7.45 μmol) was added. After addition of water (1 mL), the resulting mixture was heated at 100° C. overnight. After removal of the solvent under reduced pressure, the title compound was obtained as a crude product. It was purified by Prep-HPLC.

Workup

customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record: ord-61067d586e204fb7a77d47c19e50a546
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273068B2

Reaction notes

Loading…