Sodium Carbonate → 1,3-Bis(1,1-dimethylethyl) 2-(4'-cyano-5,2'-dimethyl[1,1'-biphenyl]-3-yl)propanedioate

HRID 341127Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[C:28]([CH3:35])[CH:27]=1)#[N:25].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>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>[C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH:3]=2)=[C:28]([CH3:35])[CH:27]=1)#[N:25]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,3-bis(1,1-dimethylethyl) 2-(3-iodo-5-methylphenyl)propanedioate (the product of Step A, 320 mg, 0.74 mmol), 4-cyano-2-methylphenylboronic acid (178 mg, 1.11 mmol), sodium carbonate (78 mg, 0.74 mmol), bis(triphenylphosphine)palladium(II) dichloride (52 mg, 0.074 mmol), dioxane (5 mL), and water (1 mL) was heated to 80° C. and stirred for 20 minutes. The reaction mixture was then cooled to room temperature, and filtered through a plug of silica gel eluting with 20% ethyl acetate in hexanes. Concentration of the eluant under reduced pressure provided a brown oil (430 mg) containing the crude product, which was used in the next step without further purification.

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationfiltered through a plug of silica gel eluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-190c29f2a4be487bbcc6f201817819a7
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895738B2

Reaction notes

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