Dimethylformamide → 2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde
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]=1Participants
Conditions
- Temperature
- -10 °C
Procedure
(5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (example 3, step A, 700 mg, 2.2 mmol) was dissolved in 30 mL tetrahydrofuran and cooled to −78° C. n-Butyllithium (3.45 mL, 1.6 M in hexane, 5.5 mmol) was added and the reaction mixture was allowed to warm to −10° C. Stirring was continued at −10° C. for 45 minutes. The reaction was cooled again to −78° C. and N,N-dimethylformamide (404 mg, 5.5 mmol) was added. The reaction mixture was slowly warmed up and quenched at 5° C. by addition of 100 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->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=267.1 (M+H+).
Workup
- additionwas added
- temperatureThe reaction was cooled again to −78° C.
- temperatureThe reaction mixture was slowly warmed up and
- customquenched at 5° C. by addition of 100 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->50:50 gradient)
Sources & evidence
- ORD record
- ord-544e2bbe812d4a5ca716b768bd9c8817
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989628B2
Reaction notes
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