Potassium Phosphate, Tribasic → (4-(5-(6-(2-acrylamidoethoxyl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)pyridin-3-yl)methyl acetate

HRID 1774634Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[C:7]([N:15]2[N:24]=[CH:23][C:22]3[C:17](=[C:18]([F:29])[CH:19]=[C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=3)[C:16]2=[O:30])=[N:8][CH:9]=[CH:10][C:11]=1B(O)O)(=[O:3])[CH3:2].Cl.[NH2:32][CH2:33][CH2:34][O:35][C:36]1[N:41]=[C:40]([NH:42][C:43]2[C:44](=[O:51])[N:45]([CH3:50])[CH:46]=[C:47](Br)[CH:48]=2)[CH:39]=[CH:38][CH:37]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O.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:1]([O:4][CH2:5][C:6]1[C:7]([N:15]2[N:24]=[CH:23][C:22]3[C:17](=[C:18]([F:29])[CH:19]=[C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=3)[C:16]2=[O:30])=[N:8][CH:9]=[CH:10][C:11]=1[C:47]1[CH:48]=[C:43]([NH:42][C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([O:35][CH2:34][CH2:33][NH:32][C:5](=[O:4])[CH:6]=[CH2:11])[N:41]=2)[C:44](=[O:51])[N:45]([CH3:50])[CH:46]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 104c (256 mg, 0.62 mmol), 3-(6-(2-aminoethoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one hydrochloride 103b (120 mg, 0.31 mmol), Pd(dppf)Cl2 (47 mg, 0.062 mmol) and K3PO4 (131 mg, 0.62 mmol) in acetonitrile (2 mL) and water (0.2 mL) was stirred at 90° C. for 3 h under N2. The mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether, PE to give 104d (160 mg) as brown solid. This material was used for the next step directly.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
washThe residue was washed with petroleum ether, PE

Sources & evidence

ORD record: ord-846e6364d3114a948ceb39793520fdf3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260415B2

Reaction notes

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