Chloroacetaldehyde → Methyl 6-bromoimidazo[1,2-a]pyridine-7-carboxylate

HRID 420520노트

반응식

HRID 420520 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([Br:10])=[CH:8][N:7]=[C:6]([NH2:11])[CH:5]=1.C([O-])(O)=O.[Na+].Cl[CH2:19][CH:20]=O>CCO>[CH3:1][O:2][C:3]([C:4]1[C:9]([Br:10])=[CH:8][N:7]2[CH:19]=[CH:20][N:11]=[C:6]2[CH:5]=1)=[O:12]

참가 물질

5

반응물 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 25307230Methyl 2-amino-5-bromoisonicotinate

생성물 1

HCID 57906576Methyl 6-bromoimidazo[1,2-a]pyridine-7-carboxylate수율 91.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-amino-5-bromo-isonicotinic acid methyl ester (500 mg, 2.16 mmol), NaHCO3 (309 mg, 3.68 mmol) and chloracetaldehyde (1.16 mL, 9.8 mmol) in EtOH (15 mL) was vigorously stirred and refluxed for 14 h. The reaction mixture was cooled to RT, concentrated under vacuum and the remaining residue was suspended in AcOEt (100 mL). The organic fraction was washed with water (2×50 mL), then dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5-100% TBME) to yield the title compound (505 mg, 1.98 mmol, 91%). MS: 255 [M+1]+; HPLC: AtRet=0.58 TLC: RF 0.16 (hexane/DCM/TBME 1:1:2).

후처리

  1. temperaturerefluxed for 14 h
  2. concentrationconcentrated under vacuum
  3. washThe organic fraction was washed with water (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5-100% TBME)

출처 및 근거

ORD 기록
ord-094f558165b94efeadd276b2003c215a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097617B2

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