Triethylamine → (E)-4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-but-3-enoic acid methyl ester

HRID 1669720Notes

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[O:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[N:7]2.C(N(CC)CC)C.[CH3:27][O:28][C:29](=[O:33])[CH2:30][CH:31]=[CH2:32].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>[CH3:27][O:28][C:29](=[O:33])[CH2:30]/[CH:31]=[CH:32]/[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[O:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[N:7]2

Participants

Conditions

Temperature: 120 °C

Procedure

(5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (400 mg, 1.3 mmol) was dissolved in 4 mL N,N-dimethylformamide. Triethylamine (167 mg, 1.7 mmol), methyl-3-butenoate (173 mg, 1.7 mmol), tri-ortho-tolylphosphin (31 mg, 0.1 mmol) and palladium acetate (11 mg, 0.05 mmol) were added. The reaction mixture was heated at 120° C. for 1 hour and quenched by addition of 50 mL water. The mixture was extracted three times with ethyl acetate (100 mL each). The organic phases were pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->75:25 gradient). (E)-4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-but-3-enoic acid methyl ester was obtained as a yellow oil (294 mg, 69%), MS: m/e=337.4 (M+H+).

Workup

customquenched by addition of 50 mL water
extractionThe mixture was extracted three times with ethyl acetate (100 mL each)
dry with materialdried with sodium sulfate
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->75:25 gradient)

Sources & evidence

ORD record: ord-d9245740770346069d2e1f6780a215a4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989628B2

Reaction notes

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