Water → HCID 86632963, compound

HRID 1095450Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:19]#[N:20])=[CH:14][C:15]=3[CH2:16][CH2:17][CH:18]=2)O1.I[C:23]1[N:27]([CH2:28][C:29]([O-:31])=[O:30])[CH:26]=[N:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O.O1CCO[CH2:41][CH2:40]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:23]1[N:27]([CH2:28][C:29]([O:31][CH2:40][CH3:41])=[O:30])[CH:26]=[N:25][CH:24]=1)=[CH:18][CH2:17][CH2:16]2)#[N:20]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 16.0 mmol of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7,8-dihydronaphthalene-2-carbonitrile, 18.0 mmol of (5-iodoimidazol-1-yl)acetate (Example 1f2), 0.74 mmol of tetrakis(triphenylphosphine)palladium(0) and 16 ml of 2M aqueous sodium carbonate solution in 100 ml of dioxane is heated at 80° C. for 5 hours. The reaction mixture is cooled, poured into water and extracted with tert-butyl methyl ether. The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The title compound is obtained as a colourless oil from the residue by flash chromatography (SiO2 60F). Rf=0.11 (dichloromethane-methanol 97:3); Rt=5.90 (gradient II).

Workup

temperatureThe reaction mixture is cooled
extractionextracted with tert-butyl methyl ether
washThe combined organic phases are washed with brine
dry with materialdried with sodium sulphate
customevaporated

Sources & evidence

ORD record: ord-d149d4047dee40119e4ac865341d4a43
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138179B2

Reaction notes

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