Cesium carbonate → HCID 118161578, compound

HRID 2203682Notes

Reaction equation

CS[C:3]([S:16][CH3:17])=[CH:4][C:5]([CH:7]1[CH:15]2[CH:8]1[CH2:9][C:10]1([CH2:14]2)[CH2:13][O:12][CH2:11]1)=[O:6].[F:18][CH:19]([F:37])[O:20][C:21]1[C:22]([NH2:36])=[N:23][CH:24]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>S1C=CC=C1C([O-])=O.[Cu+].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.O1CCCC1.O>[NH2:36][C:22]1[N:23]=[CH:24][C:25](/[C:3](/[S:16][CH3:17])=[CH:4]\[C:5]([CH:7]2[CH:15]3[CH:8]2[CH2:9][C:10]2([CH2:14]3)[CH2:13][O:12][CH2:11]2)=[O:6])=[CH:26][C:21]=1[O:20][CH:19]([F:37])[F:18]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3,3-bis(methylthio)-1-(spiro[bicyclo[3.1.0]hexane-3,3′-oxetan]-6-yl)prop-2-en-1-one (250 mg, 924 mmol) in 6:1 tetrahydrofuran/water (3.5 mL) was added 3-(difluoromethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (317 mg, 1.11 mmol), copper(I) thiophene-2-carboxylate (353 mg, 1.85 mmol), cesium carbonate (602 mg, 1.85 mmol), and bis(triphenylphosphine)palladium(II) dichloride (65 mg, 92 mmol). The reaction mixture was heated at 110° C. with microwave irradiation for 1.5 h. The reaction mixture was concentrated, and the resulting residue was purified by flash column chromatography (ethyl acetate) to afford product as a white solid (0.080 g, 23%).

Workup

concentrationThe reaction mixture was concentrated
customthe resulting residue was purified by flash column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-8705a0e5109040819c943f678c03e431
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365583B2

Reaction notes

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