Ethanol → N-[6-(8-Cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-(4-fluorophenyl)nicotinamide

HRID 1748659Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:28]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2([C:26]#[N:27])[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH2:17]2)=[CH:14][CH:15]=1)=[O:8].[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:26]([C:16]1([C:13]2[N:12]=[CH:11][C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:28]=[C:2]([C:33]4[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=4)[CH:3]=[N:4][CH:5]=3)=[CH:15][CH:14]=2)[CH2:25][CH2:24][C:19]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:18][CH2:17]1)#[N:27]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 5-bromo-N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]nicotinamide (213 mg), 4-fluorophenylboronic acid (63 mg), bis(triphenylphosphine)palladium (II) dichloride (100 mg) and sodium carbonate (636 mg) in a mixture of toluene (5 ml), ethanol (1 ml) and water (1 ml) was stirred at 100° C. for six hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography to give the titled compound (31 mg).

Workup

additionwas added
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified with column chromatography

Sources & evidence

ORD record: ord-a4c98d12a87c43ab8fc20a8df0efb0bc
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

Loading…