Acetic Acid → {2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol

HRID 1669719노트

반응식

HRID 1669719 반응식
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([CH:19]=[O:20])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19][OH:20])[N:10]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 866194932-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde

생성물 1

HCID 44218152{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde (150 mg, 0.56 mmol) was dissolved in 5 mL dichloroethan. Acetic acid (136 mg, 2.3 mmol) and sodium triacetoxy borohydride (258 mg, 1.2 mmol) were added. The reaction mixture was stirred at room temperature overnight and quenched by addition of 2N sodium carbonate solution (50 mL). 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). The title compound was obtained as a light brown solid (105 mg, 69%), MS: m/e=269.5 (M+H+).

후처리

  1. customquenched by addition of 2N sodium carbonate solution (50 mL)
  2. extractionThe mixture was extracted three times with ethyl acetate (100 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->50:50 gradient)

출처 및 근거

ORD 기록
ord-e635a2a9f43f464a90b0ecf7c801b485
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989628B2

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