Styrene → (2-Methoxy-benzyl)-[5-((E)-styryl)-quinolin-2-yl]-amine

HRID 1170072Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[CH2:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 3 mL dimethylformamide. Styrene (79 mg, 0.760 mmol), triethylamine (77 mg, 0.760 mmol), tri-o-tolylphosphine (14 mg, 0.046 mmol) and palladium(II)acetate (5 mg, 0.022 mmol) were added. The reaction mixture was stirred in a sealed tube at 100° C. for 2 h. The reaction mixture was poured into 30 mL water and extracted three times with ethyl acetate (30 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). The title compound was obtained as a light yellow solid (142 mg, 67%),

Workup

extractionextracted three times with ethyl acetate (30 mL each)
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
customevaporated
customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record: ord-35e7f1c343af4c4b80203ffb32c8ed19
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825253B2

Reaction notes

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