Methyl iodide → Methyl 6-bromo-4-iodonicotinate

HRID 1502400노트

반응식

HRID 1502400 반응식
[Br:1][C:2]1[CH:10]=[C:9]([I:11])[C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([I:11])[C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 582662986-Bromo-4-iodonicotinic acid

생성물 1

HCID 86674963Methyl 6-bromo-4-iodonicotinate수율 83%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of 6-bromo-4-iodonicotinic acid (75 mg, 0.23 mmol), potassium carbonate (63 mg, 0.46 mmol), and methyl iodide (0.017 mL, 0.27 mmol) in N,N-dimethylformamide (0.5 mL) was heated at 60° C. for 30 minutes. The cooled reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (15 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a white solid (65 mg, 83%), which was used in the next step without further purification.

후처리

  1. customThe cooled reaction mixture
  2. washwashed with water (15 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-35f745f8d0d14f11bd62fa0c65f1577e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206175B2

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