Water → 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-methyl-pyridin-4-yl]-benzoic acid methyl ester

HRID 1529213Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[C:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=1.C[CH:19]([C:21]1[CH:26]=[C:25](C(C)C)[C:24](C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=[C:23](C(C)C)[CH:22]=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH2:60].[O:61]1CCOC[CH2:62]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:62][O:61][C:19](=[O:60])[C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=2[C:9]#[C:10][C:11]2[CH:16]=[N:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The title compound is synthesized according to general procedure GP3 starting from 1.5 g (6.2 mmol) 5-(4-chloro-2-methyl-pyridin-3-ylethynyl)-pyridin-2-ylamine using 2.2 g (12.3 mmol) 4-methoxycarbonylphenyl boronic acid, 281 mg (0.31 mmol) Pd2(dba)3, 440 mg (0.92 mmol) X-Phos and 1.7 g (7.4 mmol) K3PO4 in 25 mL dioxane. The reaction mixture is stirred over night at 100° C. After cooling to RT the reaction mixture is added dropwise into water, the precipitate is filtered off. The solid is taken up in iPrOH, stirred for a few minutes, filtered off and dried under vacuum. Yield: 2.0 g (95%, residual Pd).

Workup

temperatureAfter cooling to RT the reaction mixture
filtrationthe precipitate is filtered off
stirringstirred for a few minutes
filtrationfiltered off
customdried under vacuum

Sources & evidence

ORD record: ord-cc3621f06ea34fe785dc4e9cc50a0179
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090564B2

Reaction notes

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