Cesium carbonate → 3-(2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-oxochroman-6-yl)benzonitrile

HRID 1408798Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([CH:12]1[CH2:17][CH2:16][O:15][C:14]([CH3:19])([CH3:18])[CH2:13]1)[CH2:6][C:5]2=[O:20].[C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)#[N:22].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:18][C:14]1([CH3:19])[CH2:13][CH:12]([CH:7]2[CH2:6][C:5](=[O:20])[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:27]4[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=4)[C:21]#[N:22])[CH:3]=3)[O:8]2)[CH2:17][CH2:16][O:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of crude 6-bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)chroman-4-one (460 mg, 1.36 mmol), 3-cyanophenylboronic acid (299 mg, 2.0 mmol) and Cs2CO3 (866 mg, 2.72 mmol) in 1,4-dioxane (5 mL) and H2O (1 mL) charged in a 10 mL CEM microwave test tube was added PdCl2(PPh3)2 (50 mg), then the system was degassed by sweeping N2 and capped. Then the mixture was heated to 100° C. for 10 min in a CEM microwave reactor. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel give (3-(2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-oxochroman-6-yl)benzonitrile (251 mg). MS ESI+ve m/z 362 (M+H)+.

Workup

customthe system was degassed
customcapped
customThe solvent was removed under reduced pressure
customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-6cfe2a993dde4442892bcc4d4727aefd
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921359B2

Reaction notes

Loading…