Water → HCID 23130469, compound

HRID 2080167Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.[CH3:14][N:15]1CCCC1=O.O>[C-]#N.[Zn+2].[C-]#N.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(OCC)(=O)C>[CH2:11]([O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[N:15])=[CH:3][CH:4]=1)[CH2:12][CH3:13]

Participants

Conditions

Temperature: 125 °C

Procedure

1-Bromo-4-(2-propoxy-ethyl)-benzene described in Preparation Example 195 (790 mg, 3.2 mmol), zinc cyanide (380 mg, 3.2 mmol) and tetrakis(triphenylphosphine)palladium (190 mg, 0.16 mmol) were added to N-methylpyrrolidinone (10 mL), and this mixture was stirred at 125° C. for 4 hours. This reaction mixture was allowed to cool, and water (50 mL) and ethyl acetate (50 mL) were added thereto. This mixture solution was filtered through Celite pad. The organic layer was separated, then, washed with water (3 times) and brine, and then, concentrated in vacuo. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1), and the title compound (120 mg, 0.62 mmol, 19%) was obtained as a colorless oil.

Workup

temperatureto cool
filtrationThis mixture solution was filtered through Celite pad
customThe organic layer was separated
washwashed with water (3 times) and brine
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=8:1)

Sources & evidence

ORD record: ord-b240e3d793484a6cad170a069f7e540c
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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