Potassium Carbonate → 5-(6-Cyclopropyl-2'-ethyl-[3,4']bipyridinyl-3'-ylethynyl)-pyridin-2-ylamine

HRID 1529227Notes

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.[CH:19]1([C:22]2[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][N:23]=2)[CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]1([C:22]2[N:23]=[CH:24][C:25]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=3[C:10]#[C:11][C:12]3[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=3)=[CH:26][CH:27]=2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

The title compound is synthesized according to general procedure GP3 starting from 150 mg (0.58 mmol) 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine (A-30) using 142 mg (0.87 mmoL) 2-cyclopropyl-pyrid-5-yl boronic acid, 4.5 mg (0.03 mmol) Pd(PPh3)4 and 154 mg (1.11 mmol) K2CO3 in a mixture of 6.0 mL DME and 1.5 mL water. The reaction mixture is stirred twice under microwave irradiation at 150° C. for 120 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: 68 mg (34%).

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-5ebd6687b2b047b0a3e1b41f58b6299a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090564B2

Reaction notes

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