Cesium carbonate → HCID 58197523, compound

HRID 1503442Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A 10 mL microwave tube was charged with 6′-bromo-5,7-dihydrospiro[cyclopenta[d]pyridazine-6,2′-inden]-1′(3′H)-one (0.0600 g, 0.19 mmol), 3-cyanophenylboronic acid (0.1221 g, 0.83 mmol), Cs2CO3 (0.2822 g, 0.87 mmol), 1,4-dioxane (4 mL), water (1 mL), and PdCl2(PPh3)2 (0.0360 g, 0.05 mmol). The tube was heated in a CEM microwave reactor at 110° C. for 30 min. The reaction mixture was diluted with CH2Cl2 and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ μm 19×50 mm column, 10%→90% MeOH/H2O, 0.1% CF3COOH over 8 min and then 90% MeOH/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford 0.0386 g (60%) of 3-(1′-oxo-1′,3′,5,7-tetrahydrospiro[cyclopenta[d]pyridazine-6,2′-inden]-6′-yl)benzonitrile. LC-MS tR=1.43 min in 3 min chromatography, m/z 338 (MH+).

Workup

dry with materialdried over Na2SO4
customAfter the solvent was evaporated under reduced pressure
customthe residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ μm 19×50 mm column, 10%
customover 8 min

Sources & evidence

ORD record: ord-84cede0cff8a4c3c814e2faf413378fd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212153B2

Reaction notes

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