Toluene → HCID 82013681, compound

HRID 2080103Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C([NH2:17])C1C=CC=CC=1.CC(C)([O-])C.[Na+].[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1>[CH2:30]([C:2]1[C:3]([NH2:17])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromo-benzonitrile (500 mg, 2.75 mmol), benzylamine (360 μl, 3.30 mmol), 2,2-bis(diphenylphosphino)-1,1′-binaphthyl (8.6 mg, 14 μmol), tris(dibenzylideneacetone)dipalladium(0) (19 mg, 21 μmol) and sodium tert-butoxide (370 mg, 3.85 mmol) were suspended in toluene (10 mL), and the mixture was stirred at 80° C. for 22 hours under nitrogen atmosphere. The reaction mixture was filtered through Celite pad, then, the filtrate was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=15:1), and the title compound (331 mg, 1.59 mmol, 58%) was obtained as a pale yellow oil.

Workup

filtrationThe reaction mixture was filtered through Celite pad
customthe filtrate was evaporated in vacuo
customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record: ord-8b4a80eccaaf44298d725814da782d43
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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