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

HRID 1170088노트

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HRID 1170088 반응식
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

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 67333430(5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amineHCID 178418339Butyllithium

생성물 1

HCID 866194932-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

(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+).

후처리

  1. temperatureThe reaction mixture was then cooled again to −78° C.
  2. temperatureThe mixture was then slowly warmed up
  3. customquenched with 100 mL water at 5° C
  4. extractionThe mixture was extracted three times with ethyl acetate (100 mL each)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

출처 및 근거

ORD 기록
ord-cd1a668093e948bd9dd8058f22e54c6d
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825253B2

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