Sodium Carbonate → HCID 90412812, compound

HRID 1521977Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15](I)=[CH:16][C:9]=23)[CH:7]=1.CC1(C)C(C)(C)OB([C:28]2[CH2:33][CH2:32][CH:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH:29]=2)O1.COCCOC.C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:28]4[CH2:33][CH2:32][CH:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH:29]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of Example 219A (500 mg, 1.358 mmol), ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate (495 mg, 1.766 mmol), and bis(triphenylphosphine)palladium(II) dichloride (95 mg, 0.136 mmol) in 30 mL 7:2:3 1,2-dimethoxyethane/ethanol/water was added sodium carbonate (432 mg, 4.07 mmol). The mixture was heated at 100° C. for 4 hours, cooled to room temperature, and diluted with 50 mL ethyl acetate. The mixture was washed with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was triturated with ethyl acetate and the solid was filtered and dried in vacuo to give the title compound. MS (ESI): 395.2 (M+H)+.

Workup

temperaturecooled to room temperature
washThe mixture was washed with saturated sodium bicarbonate, water and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was triturated with ethyl acetate
filtrationthe solid was filtered
customdried in vacuo

Sources & evidence

ORD record: ord-ba10667ffbe746aaabefcef924ff01e3
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073922B2

Reaction notes

Loading…