Potassium Carbonate → HCID 58235318, compound

HRID 1529222Notes

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]([NH2:20])=[N:16][C:17]=1[CH2:18][CH3:19].[F:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[C:28]([O:30][CH3:31])=[O:29].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>[CH3:31][O:30][C:28](=[O:29])[C:27]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=2[C:10]#[C:11][C:12]2[C:17]([CH2:18][CH3:19])=[N:16][C:15]([NH2:20])=[CH:14][CH:13]=2)=[CH:23][C:22]=1[F:21]

Participants

Conditions

Temperature: 130 °C

Procedure

The title compound is synthesized according to general procedure GP3 starting from 1.29 g (4.5 mmol) 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-6-ethyl-pyridin-2-ylamine (A-30) using 1.34 mg (6.8 mmol) 3-Fluoro-4-methoxycarbonylphenyl boronic acid, 1.4 g (0.9 mmol) Pd(PPh3)4 and 1.19 g (8.6 mmol) K2CO3 in a mixture of 9 mL 1,2-dimethoxyethane and 2.25 mL water. The reaction mixture is stirred twice for 30 min at 130° C. under microwave irradiation. The product is precipitated by the addition of water, filtered off and purified by chromatography on silica gel using a cyclohexane/ethyl acetate gradient. Yield: 944 mg (52%).

Workup

customThe product is precipitated by the addition of water
filtrationfiltered off
custompurified by chromatography on silica gel using a cyclohexane/ethyl acetate gradient

Sources & evidence

ORD record: ord-a4e768aa3984483a8a0356a002d052d7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090564B2

Reaction notes

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