Dimethylformamide → 2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde

HRID 1170088Notes

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([Li])CCC.CN(C)[CH:27]=[O:28]>O1CCCC1>[CH3:19][C:16]1[O:15][C:14]([CH2:13][NH:12][C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH:27]=[O:28])=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: -10 °C

Procedure

(5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (700 mg, 2.11 mmol) was dissolved in 30 mL tetrahydrofurane. n-Butyllithium solution (1.6 M in hexane, 3.45 mL, 2.16 mmol) was slowly added at −78° C. The reaction mixture was allowed to warm to −10° C. and stirred at this temperature for 45 min. The reaction mixture was then cooled again to −78° C. and dimethylformamide (404 mg, 5.53 mmol) was added. The mixture was then slowly warmed up and quenched with 100 mL water at 5° C. The mixture was extracted three times with ethyl acetate (100 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). 2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde was obtained as a brown oil (242 mg, 41%), MS: m/e=185.1 (M-methylfuran+).

Workup

temperatureThe reaction mixture was then cooled again to −78° C.
temperatureThe mixture was then slowly warmed up
customquenched with 100 mL water at 5° C
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 (cyclohexane/ethyl acetate 100:0->50:50 gradient)

Sources & evidence

ORD record: ord-cd1a668093e948bd9dd8058f22e54c6d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825253B2

Reaction notes

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