Potassium Phosphate, Tribasic → 5-(2,2'-Diethyl-[4,4']bipyridinyl-3-ylethynyl)-pyridin-2-ylamine

HRID 1529225Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[C:10]#[C:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.[CH2:19]([C:21]1[CH:26]=[C:25](B(O)O)[CH:24]=[CH:23][N:22]=1)[CH3:20].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.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]>[CH2:8]([C:4]1[C:3]([C:10]#[C:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[C:2]([C:25]2[CH:24]=[CH:23][N:22]=[C:21]([CH2:19][CH3:20])[CH:26]=2)[CH:7]=[CH:6][N:5]=1)[CH3:9]

Participants

Conditions

Temperature: 190 °C

Procedure

The title compound is synthesized according to general procedure GP3 starting from 100 mg (0.39 mmol) 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine (A-30) using 146 mg (˜60% purity, 0.58 mmoL) 2-ethyl-pyrid-4-yl boronic acid, 18 mg (0.02 mmol) Pd2(dba)3, 28 mg (0.06 mmol) XPhos and 107 mg (0.47 mmol) K3PO4 in a mixture of 6.0 mL DME. The reaction mixture is stirred twice under microwave irradiation at 190° C. for 300 min. The reaction mixture is concentrated in vaccuo and the crude product is purified by chromatography on silica gel using a DCM/MeOH-gradient. Yield: 9 mg (7%).

Workup

concentrationThe reaction mixture is concentrated in vaccuo
customthe crude product is purified by chromatography on silica gel using a DCM/MeOH-gradient

Sources & evidence

ORD record: ord-512d27e2b6a549aabb6c7f8625dca54f
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090564B2

Reaction notes

Loading…