Nitrogen → 3-(1-Oxo-1,2',3,3',5',6'-hexahydrospiro[indene-2,4'-pyran]-6-yl)benzonitrile

HRID 472958Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].Br[C:8]1[CH:21]=[C:20]2[C:11]([CH2:12][C:13]3([C:19]2=[O:22])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=1.[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)#[N:24].N#N>C(Cl)Cl.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.O.O1CCOCC1>[O:22]=[C:19]1[C:13]2([CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH2:12][C:11]2[C:20]1=[CH:21][C:8]([C:29]1[CH:30]=[C:25]([CH:26]=[CH:27][CH:28]=1)[C:23]#[N:24])=[CH:9][CH:10]=2

Participants

Conditions

Temperature: 100 °C

Procedure

To a 10 mL CEM microwave test tube was charged with Cs2CO3 (232 mg, 0.712 mmol), PdCl2(PPh3)2 (20 mg, 0.028 mmol), 6-bromo-2′,3′,5′,6′-tetrahydrospiro[indene-2,4′-pyran]-1(3H)-one (100 mg, 0.356 mmol), 3-cyanophenylboronic acid (78 mg, 0.534 mmol), dioxane (4 mL) and H2O (0.4 mL), the system was swept with N2 and capped, and heated in a CEM microwave reactor at 100° C. for 10 min. The reaction mixture was diluted with DCM, washed with brine, dried over anhydrous Na2SO4, and filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-30%) to give 42 mg of 3-(1-oxo-1,2′,3,3′,5′,6′-hexahydrospiro[indene-2,4′-pyran]-6-yl)benzonitrile. MS ESI+ve m/z 304 (M+H)+.

Workup

customcapped
washwashed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-30%)

Sources & evidence

ORD record: ord-53702cf7894f40d1bb5bc48caedd6fe2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633212B2

Reaction notes

Loading…