Potassium Phosphate, Tribasic → HCID 68442404, compound

HRID 2246937Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:13](=[O:14])[CH:12]=[C:11](OS(C2C(C)=CC=CC=2)(=O)=O)[CH2:10][CH:9]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([C:41]2[CH:42]=[CH:43][C:38]([O:37][CH3:36])=[CH:39][CH:40]=2)[CH2:10][C@H:9]1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2.75 g of 6-oxo-4-(toluene sulfonyloxy)-3,6-dihydro-2H-pyridine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester in 18 ml of tetrahydrofuran are added 1.4 g of 4-methoxyphenylboronic acid, 3.15 g of potassium phosphate, 0.12 g of ′ic′cl′hexyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (X-PHOS) and 22 mg of palladium acetate under argon. The reaction mixture is heated to 80° C. for 2 hours, cooled to room temperature, diluted with ethyl acetate and the organic phase is washed with water and dried over sodium sulfate. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a brown solid. Rf=0.35 (EtOAc-heptane 1:2); Rt=4.95.

Workup

temperaturecooled to room temperature
washthe organic phase is washed with water
dry with materialdried over sodium sulfate
customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record: ord-01efe9abd60b4958837b2870c6c45ac2
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687495B2

Reaction notes

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